SYNTHESIS OF (+ -)-TETRAHYDROMYRICOIDINE

Authors
SONG JG HESSE M
Citation
Jg. Song et M. Hesse, SYNTHESIS OF (+ -)-TETRAHYDROMYRICOIDINE, Tetrahedron, 49(31), 1993, pp. 6797-6804
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
31
Year of publication
1993
Pages
6797 - 6804
Database
ISI
SICI code
0040-4020(1993)49:31<6797:SO(->2.0.ZU;2-Z
Abstract
A total synthesis of the spermidine alkaloid (+/-)-tetrahydromyricoidi ne (6) was achieved by using two ring enlargement reactions. The diffi culties experienced in the second ring enlargement step, a transamidat ion reaction with a medium ring sized lactam bearing two bulky groups are discussed. These were overcome by altering the reaction sequence a nd the transamidation reaction was successfully carried out by at firs t deprotection of the Boc function.