Concise Total Synthesis of the Bisnorditerpene (+)‐(5β, 8α, 10α)‐8‐hydroxy‐13‐methylpodocarpa‐9(11), 13‐diene‐3, 12‐dione. Issue 8 (31st May 2016)

• Record Type: Journal Article
• Authors: Xu, Shiyan; Zhang, Mingjie; Zhang, Weiwei; Xie, Xingang; She, Xuegong
• Is Part Of: Asian journal of organic chemistry. Volume 5:Issue 8(2016)
• Page Start: 986
• Page End: 990
• Publication Date: 2016-05-31
• Subjects: cationic -- cyclization -- dearomatization -- domino -- total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201600209
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The first enantioselective total synthesis of the bisnorditerpene (+)‐(5β, 8α, 10α)‐8‐hydroxy‐13‐methylpodocarpa‐9(11), 13‐diene‐3, 12‐dione (1 ) was accomplished in 7 steps with 18.5 % overall yield from known aldehyde and chiral epoxide. Key steps of the synthesis include a cationic domino cyclization used to construct the [6, 6, 6] fused framework, and an oxidative dearomatization reaction used to form the 1, 4‐quinoid moiety. Abstract : Short and sweet : The first enantioselective total synthesis of the bisnorditerpene (+)‐(5β, 8α, 10α)‐8‐hydroxy‐13‐methylpodocarpa‐9(11), 13‐diene‐3, 12‐dione (1 ) was accomplished in 7 steps with 18.5 % overall yield from known aldehyde and chiral epoxide. Key steps of the synthesis include a cationic domino cyclization to construct the [6, 6, 6]‐fused framework, and an oxidative dearomatization reaction used to form the 1, 4‐quinoid moiety.