Novel synthesis of 12,13-seco norditerpenoid alkaloids via semipinacol rearrangement and reaction with Br-2-HOAc

Authors
Wang, FP Chen, QH Li, BG
Citation
Fp. Wang et al., Novel synthesis of 12,13-seco norditerpenoid alkaloids via semipinacol rearrangement and reaction with Br-2-HOAc, TETRAHEDRON, 57(22), 2001, pp. 4705-4712
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
22
Year of publication
2001
Pages
4705 - 4712
Database
ISI
SICI code
0040-4020(20010528)57:22<4705:NSO1NA>2.0.ZU;2-D
Abstract
Treatment of 14-methylsulfonyl pseudaconine 3 with DMF-NaOH at 150 degreesC for 10 h afforded the desired C-nor and 12,13-seco norditerpenoid alkaloid s 16 alpha -methoxyl ketone 7 (70%) and 16 beta -methoxyl ketone 8 (15%) as a pair of epimers. Reaction of 7 with Br-2-HOAc at room temperature for 1. 5-2 h produced the phenols 9 (40%), 10 (10%) and 13 (29%). Whereas, treatme nt of 8 with Br-2-HOAc under same conditions as the case for 7 gave phenoli c compound 9 (38%) besides the by-product alpha -bromoketone 14 (25%). (C) 2001 Elsevier Science Ltd. All rights reserved.