Concise synthesis of the bicyclic core of the chromoprotein antibiotics kedarcidin and neocarzinostatin by transannular reductive cyclization of a tetrayne precursor.

Authors
Myers, AG Goldberg, SD
Citation
Ag. Myers et Sd. Goldberg, Concise synthesis of the bicyclic core of the chromoprotein antibiotics kedarcidin and neocarzinostatin by transannular reductive cyclization of a tetrayne precursor., TETRAHEDR L, 39(52), 1998, pp. 9633-9636
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
39
Issue
52
Year of publication
1998
Pages
9633 - 9636
Database
ISI
SICI code
0040-4039(199812)39:52<9633:CSOTBC>2.0.ZU;2-3
Abstract
The oxygenated [7.3.0]-bicyclododecadienediyne 8 is synthesized in 9 steps from L-dimethyl tartrate. In the key transformation, transannular reductive cyclization of the potassium salt of the tetrayne alcohol 7 with NaAlH(OCH 2CH2(NCH3)(2))(3) affords the bicyclic product 8 in 50-54% yield. This sequ ence provides a rapid entry into the strained bicyclic core structures of k edarcidin md neocarzinostatin chromophores (1 and 2, respectively). (C) 199 8 Elsevier Science Ltd. All rights reserved.