Synthetic studies toward 13-oxyingenol: construction of the fully substituted tetracyclic compound

Takayuki Ohyoshi; Yamato Miyazawa; Kenta Aoki; Satomi Ohmura; Yuki Asuma; Ichiro Hayakawa; Hideo Kigoshi

doi:10.1021/ol103151k

Synthetic studies toward 13-oxyingenol: construction of the fully substituted tetracyclic compound

Org Lett. 2011 May 6;13(9):2160-3. doi: 10.1021/ol103151k. Epub 2011 Mar 29.

Authors

Takayuki Ohyoshi¹, Yamato Miyazawa, Kenta Aoki, Satomi Ohmura, Yuki Asuma, Ichiro Hayakawa, Hideo Kigoshi

Affiliation

¹ Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tennodai, Tsukuba 305-8571, Japan.

PMID: 21446676
DOI: 10.1021/ol103151k

Abstract

13-Oxyingenol and its derivatives have high levels of anti-HIV activity. A fully substituted tetracyclic skeleton of 13-oxyingenol is constructed by using spiro-cyclization and ring-closing olefin metathesis as key steps.

Publication types

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

MeSH terms

Cyclization
Diterpenes / chemical synthesis*
Heterocyclic Compounds, 4 or More Rings / chemistry*
Isomerism
Molecular Structure
Spiro Compounds / chemistry

Substances

13-oxyingenol
Diterpenes
Heterocyclic Compounds, 4 or More Rings
Spiro Compounds