Total synthesis of debromoflustramines B and E based on the intramolecular carbamoylketene-alkene [2 + 2] cycloaddition

Tsukasa Ozawa; Makoto Kanematsu; Hiromasa Yokoe; Masahiro Yoshida; Kozo Shishido

doi:10.1021/jo301817w

Total synthesis of debromoflustramines B and E based on the intramolecular carbamoylketene-alkene [2 + 2] cycloaddition

J Org Chem. 2012 Oct 19;77(20):9240-9. doi: 10.1021/jo301817w. Epub 2012 Oct 9.

Authors

Tsukasa Ozawa¹, Makoto Kanematsu, Hiromasa Yokoe, Masahiro Yoshida, Kozo Shishido

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan.

PMID: 23013172
DOI: 10.1021/jo301817w

Abstract

Total synthesis of debromoflustramines B and E has been accomplished by using a platinum-catalyzed addition reaction of o-aminophenylboronic acid with the allene and an intramolecular carbamoylketene-alkene [2 + 2] cycloaddition for the construction of the basic carbon framework of the target alkaloids as the key steps.

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Alkenes / chemistry*
Cyclization
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Stereoisomerism

Substances

1-methyl-3a-(3-methylbut-2-enyl)-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indole
Alkaloids
Alkenes
Indole Alkaloids
debromoflustramine B