Studies on the total synthesis of formamicin: synthesis of the C(1)-C(11) fragment

N A Powell; W R Roush

doi:10.1021/ol0069610

Studies on the total synthesis of formamicin: synthesis of the C(1)-C(11) fragment

Org Lett. 2001 Feb 8;3(3):453-6. doi: 10.1021/ol0069610.

Authors

N A Powell¹, W R Roush

Affiliation

¹ Department of Chemistry, University of Michigan, 930 North University, Ann Arbor, Michigan 48109, USA.

PMID: 11428037
DOI: 10.1021/ol0069610

Abstract

[figure: see text] An efficient and highly concise synthesis of 6, corresponding to the C(1)-C(11) fragment of formamicin (1), has been accomplished by a route utilizing a diastereoselective lactate aldol reaction to set the C(6) tertiary ether and the TES-OTf mediated transketalization of the C(6) tertiary methoxymethyl ether and the C(25) PMB ether to set the seven-membered methylene acetal unit (see 37-->38).

Publication types

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

MeSH terms

Actinomycetales / chemistry
Anti-Bacterial Agents / chemical synthesis*
Antifungal Agents / chemical synthesis*
Macrolides*

Substances

Anti-Bacterial Agents
Antifungal Agents
Macrolides
formamicin

Abstract

Publication types

MeSH terms

Substances

Grants and funding