Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure

K I Takao; T Sasaki; T Kozaki; Y Yanagisawa; K I Tadano; A Kawashima; H Shinonaga

doi:10.1021/ol016960n

Syntheses and absolute stereochemistries of UPA0043 and UPA0044, cytotoxic antibiotics having a p-quinone-methide structure

Org Lett. 2001 Dec 27;3(26):4291-4. doi: 10.1021/ol016960n.

Authors

K I Takao¹, T Sasaki, T Kozaki, Y Yanagisawa, K I Tadano, A Kawashima, H Shinonaga

Affiliation

¹ Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 11784200
DOI: 10.1021/ol016960n

Abstract

The first syntheses of new antibiotics UPA0043 and UPA0044 were accomplished starting from commercially available 18beta-glycyrrhetinic acid and vanillin. The present syntheses involve the coupling of a sesquiterpenoid aldehyde and an aryllithium, the stereoselective formation of a p-quinone-methide system, and regioselective intramolecular cyclization via an epoxy ring opening. [reaction: see text]

MeSH terms

Antibiotics, Antineoplastic / chemical synthesis*
Antibiotics, Antineoplastic / chemistry*
Antibiotics, Antineoplastic / pharmacology
Indolequinones*
Indoles / chemistry*
Molecular Structure
Quinones / chemical synthesis*
Quinones / chemistry*
Quinones / pharmacology

Substances

Antibiotics, Antineoplastic
Indolequinones
Indoles
Quinones
UPA0043
UPA0044
quinone methide