Total Synthesis of Aquatolide: Wolff Ring Contraction and Late-Stage Nozaki-Hiyama-Kishi Medium-Ring Formation

被引：26

作者：

Wang, Bin ^{[1
]}

Xie, Yuanzhen ^{[1
]}

Yang, Qin

Zhang, Guozhu ^{[2
]}

Gu, Zhenhua ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 20期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; SESQUITERPENE LACTONE; KINETIC RESOLUTION; CARBONYL ADDITION; ASTERISCUNOLIDE-D; SOLANOECLEPIN; CHLORIDE; OLEFINS; (+)-ASTERISCANOLIDE; CYCLOPENTENONES;

D O I：

10.1021/acs.orglett.6b02767

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the highly strained natural product aquatolide has been achieved. The synthesis featured a photoinduced Wolff ring contraction reaction for the construction of bicyclo[2.1.1]hexane from diazo compound with a bicydo[2.2.1]heptane skeleton. The eight-membered enone was built by a late-stage intramolecular Nozaki-Hiyama-Kishi vinylation reaction of steric bulky vinyl iodide and aldehyde.

引用

页码：5388 / 5391

页数：4

共 44 条

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