An approach to the anhydride unit of CP-225,917 and CP-263,114

Authors
Clive, DLJ Sun, SY Gagliardini, V Sano, MK
Citation
Dlj. Clive et al., An approach to the anhydride unit of CP-225,917 and CP-263,114, TETRAHEDR L, 41(33), 2000, pp. 6259-6263
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
33
Year of publication
2000
Pages
6259 - 6263
Database
ISI
SICI code
0040-4039(20000812)41:33<6259:AATTAU>2.0.ZU;2-4
Abstract
Compound 1, representing the core structure of CP-225,917, including the an hydride subunit, was prepared by an approach involving siloxy-Cope rearrang ement of the strained lactone 18, in which C(15) of the anhydride is alread y present. The C(14) carbon was introduced at a later stage with the Tebbe reagent. Further elaboration gave homoallylic alcohol 25, which was convert ed into epoxy aldehyde 27, and then into furan 28. This was transformed eff iciently into 1 by the successive action of singlet oxygen, DBU and TPAP. ( C) 2000 Elsevier Science Ltd. All rights reserved.