A Total Synthesis of (-)-Nardoaristolone B

被引：5

作者：

Ople, Rohini S. ^{[1
,2
]}

Handore, Kishor L. ^{[1
,2
]}

Kamat, Nidhi S. ^{[1
]}

Reddy, D. Srinivasa ^{[1
,2
]}

机构：

[1] CSIR Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110020, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 22期

关键词：

Natural products; Total synthesis; Chiral pool; Nardoaristolone B; Cyclopropanation; NARDOSTACHYS-CHINENSIS ROOTS; FORMOSAN SUBTERRANEAN TERMITE; GUAIANE-TYPE; SESQUITERPENOIDS; ARISTOLONE; NOOTKATONE; VINYLATION; OXIDATION; ANALOGS; KETONES;

D O I：

10.1002/ejoc.201600538

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective total synthesis of (-)-Nardoaristolone B, a nor-aristolane sesquiterpenoid natural product with an unusual 3/5/6 tricyclic ring system is described. The highlights of the present work includes use of (+)-(R)-Pulegone as a chiral-pool starting material, ring-closing metathesis, allylic oxidation and stereoselective cyclopropanation. In addition, a new analogue of Nardoaristolone B (minor product from the final step) was isolated in pure form and fully characterized with the help of single-crystal X-ray analysis.

引用

页码：3804 / 3808

页数：5

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