A NEW STEREOSELECTIVE SYNTHESIS OF LADYBUG DEFENSE ALKALOID PRECOCCINELLINE

Authors
YUE CW NICOLAY JF ROYER J HUSSON HP
Citation
Cw. Yue et al., A NEW STEREOSELECTIVE SYNTHESIS OF LADYBUG DEFENSE ALKALOID PRECOCCINELLINE, Tetrahedron, 50(10), 1994, pp. 3139-3148
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
10
Year of publication
1994
Pages
3139 - 3148
Database
ISI
SICI code
0040-4020(1994)50:10<3139:ANSSOL>2.0.ZU;2-3
Abstract
We have accomplished a new stereoselective synthesis of precoccinellin e 1 in six steps from the chiral synthon 6 with a overall yield of 31 %. The main feature of this synthesis is the asymmetric synthesis of t he trans 2,6-keto-acetal piperidine 14 which assures a stereospecific cyclisation in the construction of key intermediate ketone 4.