Total Synthesis of (-)-Ceforalide B and (-)-Cephanolides B-D

被引：17

作者：

Sun, Zhongliu ^{[1
]}

Fan, Xin ^{[1
]}

Sun, Zezhong ^{[1
]}

Li, Zhijie ^{[1
]}

Niu, Lihua ^{[1
]}

Guo, Hao ^{[1
]}

Ren, Zhiqiang ^{[1
]}

Wang, Yunxia ^{[1
]}

Hu, Xiangdong ^{[1
]}

机构：

[1] Northwest Univ, Dept Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem Minist Educ C, Xian 710127, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 41期

基金：

中国国家自然科学基金;

关键词：

NORDITERPENOIDS; HAINANOLIDOL;

D O I：

10.1021/acs.orglett.2c02679

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Ceforalide B (1) and (-)-cephanolides B-D (2-4) are benzenoid cephanolide diterpenoids possessing the same pentacyclic skeleton, which contains three C13-C15 substituent patterns and different benzylic oxidation states. An olefination/67r-electrocyclization/oxidative aromatization cascade has been verified as divergent access to three C13-C15 patterns. The benzylic aerobic oxidations enabled by the Co(OAc)2middot4H2O/ bromide salt/O2/PPh3/N-hydroxyphthalimide system have been developed to deliver expected site-selectivity and different oxidation states. Through the divergent strategy, total synthesis of (-)-ceforalide B and (-)-cephanolides B-D is accomplished.

引用

页码：7507 / 7511

页数：5

共 9 条

[1] Synthesis of the ACDE tetracyclic skeleton in ceforalide B
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[2] Total Synthesis of the Cephalotaxus Norditerpenoids (±)-Cephanolides A-D
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[3] Asymmetric Total Syntheses of Cephalotane-Type Diterpenoids Cephanolides A-D
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[4] Total Synthesis of Norcembrenolide B and Scabrolide D
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[7] Total Synthesis of (+)-Mannolide B
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[8] Total Syntheses of Scabrolide A and Nominal Scabrolide B
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[9] Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system
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