Synthesis of a common key intermediate for (-)-tetrodotoxin and its analogs

Authors
Nishikawa, T Asai, M Ohyabu, N Yamamoto, N Fukuda, Y Isobe, M
Citation
T. Nishikawa et al., Synthesis of a common key intermediate for (-)-tetrodotoxin and its analogs, TETRAHEDRON, 57(18), 2001, pp. 3875-3883
Citations number
43
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
18
Year of publication
2001
Pages
3875 - 3883
Database
ISI
SICI code
0040-4020(20010430)57:18<3875:SOACKI>2.0.ZU;2-7
Abstract
A key intermediate for tetrodotoxin and its analogs such as (-)-5,11 -dideo xytetrodotoxin was stereoselectively synthesized from a chiral starting mat erial, levoglucosenone, via Diels-Alder reaction and the Overman rearrangem ent as key steps. The Overman rearrangement of the precursor bearing hydrox y group of C-8 was also described. (C) 2001 Elsevier Science Ltd. All right s reserved.