A stereocontrolled route to 2-substituted chromans

Authors
Hodgetts, KJ
Citation
Kj. Hodgetts, A stereocontrolled route to 2-substituted chromans, TETRAHEDR L, 41(44), 2000, pp. 8655-8659
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
44
Year of publication
2000
Pages
8655 - 8659
Database
ISI
SICI code
0040-4039(20001028)41:44<8655:ASRT2C>2.0.ZU;2-8
Abstract
A two-step synthesis of 2-substituted chromans of high enantiomeric purity is described. Mitsunobu reaction of homochiral halopropanols 10 with 2-brom ophenol (9), followed by treatment with n-butyl-lithium under Parham cycloa lkylation conditions generates 2-substituted chromans 7. The methodology wa s applied to the synthesis of the natural product tephrowatsin E (5) and th e antiviral BW683C (6). (C) 2000 Elsevier Science Ltd. All rights reserved.