Formal total synthesis of neocarzinostatin chromophore

Shoji Kobayashi; Makiko Hori; Guang Xing Wang; Masahiro Hirama

doi:10.1021/jo052031o

Formal total synthesis of neocarzinostatin chromophore

J Org Chem. 2006 Jan 20;71(2):636-44. doi: 10.1021/jo052031o.

Authors

Shoji Kobayashi¹, Makiko Hori, Guang Xing Wang, Masahiro Hirama

Affiliation

¹ Department of Chemistry, Graduate Schools of Science, Tohoku University, Sendai 980-8578, Japan. koba@c.s.osakafu-u.ac.jp

PMID: 16408974
DOI: 10.1021/jo052031o

Abstract

[reaction: see text] An efficient route to the neocarzinostatin chromophore aglycon has been developed. The present strategy involves a stereoselective intramolecular acetylide-aldehyde cyclization to form the C5-C6 bond, followed by efficient installation of alpha-epoxide, naphthoate, and carbonate functionalities. The C8-C9-olefin was introduced by using the Martin sulfurane dehydration reaction to furnish the highly reactive aglycon.

Publication types

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

MeSH terms

Enediynes
Indicators and Reagents
Models, Molecular
Molecular Conformation
Zinostatin / analogs & derivatives*
Zinostatin / chemical synthesis*
Zinostatin / chemistry

Substances

Enediynes
Indicators and Reagents
neocarzinostatin chromophore
Zinostatin