Asymmetric Total Synthesis of (-)-Kravanhin B

Zhuliang Zhong; Donghui Ma; Gaoyuan Zhao; Huilin Li; Dengyu Xu; Xingang Xie; Xuegong She

doi:10.1002/asia.201500860

Asymmetric Total Synthesis of (-)-Kravanhin B

Chem Asian J. 2015 Dec;10(12):2599-603. doi: 10.1002/asia.201500860. Epub 2015 Sep 23.

Authors

Zhuliang Zhong¹, Donghui Ma¹, Gaoyuan Zhao¹, Huilin Li¹, Dengyu Xu¹, Xingang Xie¹, Xuegong She^{2

3}

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China.
² State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. China. shexg@lzu.edu.cn.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300071, P. R. China. shexg@lzu.edu.cn.

PMID: 26398294
DOI: 10.1002/asia.201500860

Abstract

The first asymmetric total synthesis of kravanhin B has been accomplished with a linear reaction sequence of 13 steps starting from (R)-(-)-carvone. The synthesis features an intramolecular aldol cyclization to construct the desired cis-fused decalin skeleton and an acid-catalyzed dehydration and olefin isomerization to install the γ-butenolide ring.

Keywords: aldol reaction; asymmetric synthesis; total synthesis; trans-anti-cis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives
4-Butyrolactone / chemistry
Aldehydes / chemistry
Catalysis
Cyclization
Cyclohexane Monoterpenes
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Monoterpenes / chemistry
Stereoisomerism

Substances

Aldehydes
Cyclohexane Monoterpenes
Diterpenes
Monoterpenes
kravanhin B
carvone
3-hydroxybutanal
butenolide
4-Butyrolactone