Synthesis of natural products containing highly strained trans-fused bicyclo[3.3.0]octane: historical overview and future prospects

被引:19
|
作者
Zhang, Wen [1 ,2 ]
Li, Lingzi [1 ,2 ]
Li, Chuang-Chuang [1 ]
机构
[1] Southern Univ Sci & Technol SUSTech, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
[2] Southern Univ Sci & Technol SUSTech, Guangdong Prov Key Lab Catalysis, Dept Chem, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; ALKOXY-DIRECTED CYCLIZATION; BIOLOGICAL EVALUATION; CORE; SESQUITERPENES; EPOXYDICTYMENE; REARRANGEMENT; PALAUAMINE; DITERPENE; DYNEMICIN;
D O I
10.1039/d0cs01471k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Owing to high strain energy, molecules with trans-fused bicyclo[3.3.0]octane ring systems are very difficult to synthesize, and there are very few approaches to access them. Recently, a number of natural products with such ring systems have been made by the synthetic community. However, there has been no review in this field before. This review provides a systematic and comprehensive discussion on the synthesis of natural products containing trans-fused bicyclo[3.3.0]octanes and the historical context of this work. The prospects for future research in this field are also discussed. Covering the literature before 2021, this review aims to offer a helpful reference for total synthesis of highly strained natural products containing trans-fused bicyclo[3.3.0]octane ring systems.
引用
收藏
页码:9430 / 9442
页数:13
相关论文
共 9 条
  • [1] Photoinduced Intramolecular Cyclization of Acylsilanes Bearing a Boronate Moiety: Construction of a Highly Strained trans-Fused Bicyclo[3.3.0]octane Skeleton
    Yamaguchi, Kohei
    Shimizu, Tsukasa
    Miura, Arihito
    Ishida, Kento
    Kusama, Hiroyuki
    [J]. ORGANIC LETTERS, 2022, 24 (31) : 5807 - 5811
  • [2] SYNTHESIS AND X-RAY CRYSTAL-STRUCTURES OF TRICYCLIC KETONE CONTAINING TRANS-FUSED BICYCLO[3.3.0]OCTANE UNIT
    SAITOH, F
    MORI, M
    OKAMURA, K
    DATE, T
    [J]. TETRAHEDRON, 1995, 51 (15) : 4439 - 4446
  • [3] Bifunctional reagents in organic synthesis: Stereocontrolled methods for the syntheses of functionalized trans-fused bicyclo[3.3.0]octane and bicyclo[4.3.0]nonane systems
    Piers, E
    Kaller, AM
    [J]. TETRAHEDRON LETTERS, 1996, 37 (33) : 5857 - 5860
  • [4] INTRAMOLECULAR 1,3-DIYL TRAPPING REACTIONS - TOTAL SYNTHESIS OF (+/-)-HYPNOPHILIN AND (+/-)-CORIOLIN - FORMATION OF THE TRANS-FUSED BICYCLO[3.3.0]OCTANE RING-SYSTEM
    VANHIJFTE, L
    LITTLE, RD
    PETERSEN, JL
    MOELLER, KD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21): : 4647 - 4661
  • [5] SYNTHESES AND X-RAY CRYSTAL-STRUCTURES OF TRICYCLIC KETONES CONTAINING TRANS-FUSED AZABICYCLO[3.3.0]OCTANE UNITS
    MORI, M
    SAITOH, F
    UESAKA, N
    OKAMURA, K
    DATE, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17): : 4993 - 4998
  • [6] Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate
    Zancanella, Manuel A.
    Romo, Daniel
    [J]. ORGANIC LETTERS, 2008, 10 (17) : 3685 - 3688
  • [7] CHEMISTRY OF BENT BONDS .16. REACTIONS OF TRANS-FUSED CYCLOPROPANES - SYNTHESIS AND SOLVOLYSIS OF 4-HYDROXY-TRANS-BICYCLO[5.1.0]OCTANE PARA BROMOBENZENESULFONATE
    GASSMAN, PG
    SETER, J
    WILLIAMS, FJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) : 1673 - &
  • [8] Intramolecular [3+2] annulation of allenylsilane-enes: Direct synthesis of highly strained trans-fused 5/5 ring systems
    Lv, Na
    Han, Jing-Chun
    Zhang, Peng
    Huang, Yu-Rou
    Xu, Zi-Xun
    Xu, Kunhua
    Wang, Xin-Feng
    Li, Xin
    Chung, Lung Wa
    Li, Chuang-Chuang
    [J]. CHEM, 2024, 10 (01):
  • [9] Highly enantioselective total synthesis of natural epoxydictymene. An alkoxy-directed cyclization route to highly strained trans-oxabicyclo[3.3.0]octanes
    Paquette, LA
    Sun, LQ
    Friedrich, D
    Savage, PB
    [J]. TETRAHEDRON LETTERS, 1997, 38 (02) : 195 - 198