Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A

Masato Nozawa; Yuhki Suka; Takashi Hoshi; Toshio Suzuki; Hisahiro Hagiwara

doi:10.1021/ol800101v

Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A

Org Lett. 2008 Apr 3;10(7):1365-8. doi: 10.1021/ol800101v. Epub 2008 Mar 1.

Authors

Masato Nozawa¹, Yuhki Suka, Takashi Hoshi, Toshio Suzuki, Hisahiro Hagiwara

Affiliation

¹ Graduate School of Science and Technology, Niigata University, 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan.

PMID: 18311991
DOI: 10.1021/ol800101v

Abstract

Total synthesis of salvinorin A (1), a neoclerodane diterpenoid having the most potent hallucinogenic activity and a selective kappa-opioid agonist, was completed in 20 steps starting from enantiomerically pure hydroxy-Wieland-Miescher ketone 5.

Publication types

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

MeSH terms

Diterpenes, Clerodane / chemical synthesis*
Diterpenes, Clerodane / chemistry
Hallucinogens / chemical synthesis*
Hallucinogens / chemistry
Molecular Structure
Plants, Medicinal / chemistry
Salvia / chemistry
Stereoisomerism

Substances

Diterpenes, Clerodane
Hallucinogens
salvinorin A