Total synthesis of (+/-)-flustramines A and C, (+/-)-flustramide A, and (-)- and (+)-debromoflustramines A

Tomomi Kawasaki; Masashi Shinada; Mayu Ohzono; Atsuyo Ogawa; Romi Terashima; Masanori Sakamoto

doi:10.1021/jo800984a

Total synthesis of (+/-)-flustramines A and C, (+/-)-flustramide A, and (-)- and (+)-debromoflustramines A

J Org Chem. 2008 Aug 1;73(15):5959-64. doi: 10.1021/jo800984a. Epub 2008 Jun 25.

Authors

Tomomi Kawasaki¹, Masashi Shinada, Mayu Ohzono, Atsuyo Ogawa, Romi Terashima, Masanori Sakamoto

Affiliation

¹ Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. kawasaki@my-pharm.ac.jp

PMID: 18576686
DOI: 10.1021/jo800984a

Abstract

Here we describe the efficient total synthesis of the three title hexahydropyrrolo[2,3-b]indole alkaloids and debromo derivative from readily available indolin-3-ones using key domino reactions, olefination-isomerization-Claisen rearrangement (OIC), and reductive cyclization (RC). (+/-)-Flustramine C (5) was synthesized in five steps from 6-bromoindolin-3-one 9 via a key intermediate 13a. (+/-)-Flustramine A (1) has been obtained by reduction of flustramide A (6), which has been prepared in five steps from 13a. (+/-)-Debromoflustramine A (19) was provided in a similar manner from 13b. The (-)- and (+)-enantiomers of 19 were synthesized through optical resolution of (+/-)-carboxylic acid 17b using (R)-4-phenyloxazolidin-2-one.

Publication types

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

MeSH terms

Bromine Compounds / chemical synthesis*
Bromine Compounds / chemistry
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure

Substances

Bromine Compounds
Indole Alkaloids
flustramide A
flustramine C