First enantioselective total synthesis of the endogenous natriuretic agentLLU-alpha

Authors
Jung, ME MacDougall, JM
Citation
Me. Jung et Jm. Macdougall, First enantioselective total synthesis of the endogenous natriuretic agentLLU-alpha, TETRAHEDR L, 40(35), 1999, pp. 6339-6342
Citations number
16
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
35
Year of publication
1999
Pages
6339 - 6342
Database
ISI
SICI code
0040-4039(19990827)40:35<6339:FETSOT>2.0.ZU;2-C
Abstract
The endogenous natriuretic agent LLU-alpha, 1, has been synthesized from ge raniol 4 in 13 steps and 18% overall yield. The two key steps are a Gassman -Sato process to give the phenol 8 and cyclization of the triol 10 with aci d to give the chroman 12 with retention of configuration at the tertiary al cohol center. Final oxidation gave 1. (C) 1999 Elsevier Science Ltd. All ri ghts reserved.