Nodulisporic acid A synthetic studies. 2. Construction of an eastern hemisphere subtarget

A B Smith 3rd; Y S Cho; H Ishiyama

doi:10.1021/ol016888t

Nodulisporic acid A synthetic studies. 2. Construction of an eastern hemisphere subtarget

Org Lett. 2001 Nov 29;3(24):3971-4. doi: 10.1021/ol016888t.

Authors

A B Smith 3rd¹, Y S Cho, H Ishiyama

Affiliation

¹ Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu

PMID: 11720582
DOI: 10.1021/ol016888t

Abstract

In this, the second of two Letters, we describe an effective assembly of (+)-4, an eastern hemisphere subtarget comprising the FGH rings of (+)-nodulisporic acid A (1) (17 steps, 9% overall yield). Central to the synthesis is a Koga three-component conjugate addition-alkylation sequence which secures the trans orientation of the vicinal quaternary methyl groups. [reaction: see text]

Publication types

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

MeSH terms

Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure

Substances

Indoles
nodulisporic acid A

Grants and funding

GM-29028/GM/NIGMS NIH HHS/United States