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In many cases, compared to an intermolecular Diels-Alder reaction, an intramolecular variant is not necessarily manageable and predictable enough to control the selectivities of cycloaddition such as regio-, endo/exo-, or π-facial selectivity

Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

CHEMICAL REVIEWS, no. 12.0 (2006): 4779-4807

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摘要

Ken-ichi Takao, was born in Tokyo, Japan, in 1967. He received his Ph.D. in 1995 from Keio University under the direction of Professor Kin-ichi Tadano. Then he worked at Sagami Chemical Research Center for one year. From 1996 to 1998, he joined Science University of Tokyo (Professor Susumu Kobayashi) as an instructor. In 1998, he moved to...更多

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简介
  • Ken-ichi Takao, was born in Tokyo, Japan, in 1967. He received his Ph.D. in 1995 from Keio University under the direction of Professor Kin-ichi Tadano.
  • Kin-ichi Tadano was born in Chiba Prefecture, Japan, in 1948
  • He received his Ph.D. degree from Keio University in 1977 under the supervision of Professor Tetsuo Suami on the synthetic studies of carbocyclic nucleosides.
  • Ryosuke Munakata was born in 1977 in Takamatsu, Japan
  • He studied chemistry at Keio University and received his Ph.D. degree in 2004 for his research on total synthesis of macquarimicins under the supervision of Professor Kin-ichi Tadano.
重点内容
  • Ken-ichi Takao, was born in Tokyo, Japan, in 1967
  • Shea and co-workers have demonstrated the significance of the type 2 IMDA reaction in their total synthesis of (()-12 (Scheme 2).6 2-Methyl-3-(4-oxo-5-hexenyl)1,3-butadiene 6 underwent an IMDA reaction in the presence of Lewis acid (Et2AlCl at room temperature), providing the bridged bicyclic adduct 7 (70% yield)
  • In many cases, compared to an intermolecular Diels-Alder reaction, an intramolecular variant (IMDA reaction) is not necessarily manageable and predictable enough to control the selectivities of cycloaddition such as regio, endo/exo, or π-facial selectivity
  • The literature contains welldesigned IMDA reaction approaches for the stereoselective construction of the formidable core skeletons found in a variety of natural products
  • Such impressive and elegant precedents of natural product synthesis will continue to stimulate the interest of synthetic chemists
  • Sophisticated natural product synthesis shows the potency of organic synthesis and frequently offers conceptual innovation for current organic chemistry
结果
  • The intramolecular macroallylation of was achieved using Cs2CO3 as a base under high dilution conditions to provide unsaturated aldehyde after oxidation of the allylic alcohol moiety of the resulting 13-membered TCC-macrocyclic triene product.
  • Treatment of this carbocyclic substrate with MeAlCl2 in dichloromethane (23 °C) provided a TSC-fused tricyclic compound (75%) exclusively.
  • The introduction of the C2-C3 double bond into 267 initiated a sequence of transannular cycloadditions, culminating in the formation of 269 as a single isolable diastereomer (63% yield) via the R, ,γ,δunsaturated macrocyclic compound 268
结论
  • In the progress of modern organic synthesis, especially in the field of natural product synthesis, the role of Diels-Alder reactions for the construction of cyclic carbon framework is tremendous.
  • As evidenced by a huge amount of literature, the incorporation of Diels-Alder reactions in the synthetic scheme frequently makes synthetic manipulation facile and concise.
  • The literature contains welldesigned IMDA reaction approaches for the stereoselective construction of the formidable core skeletons found in a variety of natural products.
  • Such impressive and elegant precedents of natural product synthesis will continue to stimulate the interest of synthetic chemists.
  • Sophisticated natural product synthesis shows the potency of organic synthesis and frequently offers conceptual innovation for current organic chemistry
总结
  • Introduction:

    Ken-ichi Takao, was born in Tokyo, Japan, in 1967. He received his Ph.D. in 1995 from Keio University under the direction of Professor Kin-ichi Tadano.
  • Kin-ichi Tadano was born in Chiba Prefecture, Japan, in 1948
  • He received his Ph.D. degree from Keio University in 1977 under the supervision of Professor Tetsuo Suami on the synthetic studies of carbocyclic nucleosides.
  • Ryosuke Munakata was born in 1977 in Takamatsu, Japan
  • He studied chemistry at Keio University and received his Ph.D. degree in 2004 for his research on total synthesis of macquarimicins under the supervision of Professor Kin-ichi Tadano.
  • Results:

    The intramolecular macroallylation of was achieved using Cs2CO3 as a base under high dilution conditions to provide unsaturated aldehyde after oxidation of the allylic alcohol moiety of the resulting 13-membered TCC-macrocyclic triene product.
  • Treatment of this carbocyclic substrate with MeAlCl2 in dichloromethane (23 °C) provided a TSC-fused tricyclic compound (75%) exclusively.
  • The introduction of the C2-C3 double bond into 267 initiated a sequence of transannular cycloadditions, culminating in the formation of 269 as a single isolable diastereomer (63% yield) via the R, ,γ,δunsaturated macrocyclic compound 268
  • Conclusion:

    In the progress of modern organic synthesis, especially in the field of natural product synthesis, the role of Diels-Alder reactions for the construction of cyclic carbon framework is tremendous.
  • As evidenced by a huge amount of literature, the incorporation of Diels-Alder reactions in the synthetic scheme frequently makes synthetic manipulation facile and concise.
  • The literature contains welldesigned IMDA reaction approaches for the stereoselective construction of the formidable core skeletons found in a variety of natural products.
  • Such impressive and elegant precedents of natural product synthesis will continue to stimulate the interest of synthetic chemists.
  • Sophisticated natural product synthesis shows the potency of organic synthesis and frequently offers conceptual innovation for current organic chemistry
基金
  • Some total syntheses achieved in the authors’ group cited in this review were supported by Grantsin-Aid for Scientific Research on Priority Areas (A), “Targeted Pursuit of Challenging Bioactive Molecules (13024266)” and “Creation of Biologically Functional Molecules (17035075)”, and by the 21st Century COE program “KEIO Life Conjugated Chemistry” from the Ministry of Education, Culture, Sports, Science, and Technology of Japan
研究对象与分析
stereogenic centers: 7
Neither 80 nor 81 was identical to natural pseudopteroxazole, indicating the need for a revision of the structure. (-)-Ophirin B (87) is a cladiellane diterpenoid having a unique oxatricyclic ring system with seven stereogenic centers.46. Quite recently, Crimmins and Brown reported the total synthesis of (-)-87 using an IMDA strategy (Scheme 15).[47]

newly introduced stereogenic centers: 3
Reaction of 198 with vinyl tributylstannane in the presence of a Pd(0) catalyst produced the intermediary Stille coupling product 199, which spontaneously gave rise to an IMDA reaction, providing the cycloadduct 200 as a single product (68% yield). In this sequential Stille/Diels-Alder reaction, the single stereocenter existing in the substrate 198 defined the absolute and relative stereochemistry of the three newly introduced stereogenic centers in 200. From the tricyclic compound 200, ring-closing metathesis reactions were employed twice to form the 13- and 8-membered rings in 202 via 201, eventually leading to the natural product (+)-202

stereogenic centers: 12
FR182877 (263) exhibits remarkable microtubule stabilizing activity similar to the mode of action studied for paclitaxel, and it shows potent cytotoxicity toward multiple tumor cell lines.138. The highly carbon- and oxygen-functionalized hexacyclic core structure of 263 comprises 12 stereogenic centers and a strained double bond through the bridgehead position. Sorensen and co-workers have proposed that the structure of 263 might arise from a polyunsaturated linear biosynthetic intermediate by a cascade of intramolecular Diels-Alder reactions.[139]

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