Intramolecular Nozaki-Hiyama-Kishi reactions and Ln(III)-catalyzed allylicrearrangement as the key steps towards 10-membered ring enediynes

Authors
Dai, WM Wu, AX Hamaguchi, W
Citation
Wm. Dai et al., Intramolecular Nozaki-Hiyama-Kishi reactions and Ln(III)-catalyzed allylicrearrangement as the key steps towards 10-membered ring enediynes, TETRAHEDR L, 42(25), 2001, pp. 4211-4214
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
25
Year of publication
2001
Pages
4211 - 4214
Database
ISI
SICI code
0040-4039(20010618)42:25<4211:INRALA>2.0.ZU;2-X
Abstract
A general and facile synthesis of the 3-substituted 10-membered ring enediy nes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catal yzed rearrangement of allylic alkoxyacetates as the key steps. This work pr ovides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-d iynes, which can be converted into the bioactive enediynes under physiologi cal conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.