Syntheses without protection: a three-step synthesis of optically active clavicipitic acid by utilizing biomimetic synthesis of 4-bromotryptophan

Authors
Yokoyama, Y Hikawa, H Mitsuhashi, M Uyama, A Murakami, Y
Citation
Y. Yokoyama et al., Syntheses without protection: a three-step synthesis of optically active clavicipitic acid by utilizing biomimetic synthesis of 4-bromotryptophan, TETRAHEDR L, 40(44), 1999, pp. 7803-7806
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
44
Year of publication
1999
Pages
7803 - 7806
Database
ISI
SICI code
0040-4039(19991029)40:44<7803:SWPATS>2.0.ZU;2-R
Abstract
The optically active clavicipitic acid (4), an ergot alkaloid, was synthesi zed by a three-step sequence from 4-bromoindole (1). The reaction of 1 with dl-serine (2) in the presence of Ac2O followed by enzymatic kinetic resolu tion gave (S)-4-bromotryptophan (3). The Heck reaction of 3 with 1,1-dimeth ylallylalcohol in aqueous media gave clavicipitic acid in one-pot. (C) 1999 Elsevier Science Ltd. All rights reserved.