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Total synthesis of prostaglandins. V. A synthesis of (−)-prostaglandin E2 via a totally asymmetric process.

✍ Scribed by J.B. Heather; Rattan Sood; Philip Price; George P. Peruzzotti; Sang.S. Lee; Hsu Lee Lan-Fong; Charles J. Sih

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 225 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)87625-5

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✦ Synopsis

We wish to report the synthesis of prostaglandin E2 (PGE2, &) via conjugate addition of the vinyl cupratez, derived from trans-3(E)-(l-ethoxyethoxy)l-iodo-l-octene (3b), to 2-(6-carbomethoxy-~-2-hexenyl)-4(R)-(2-tetrahydropyranyloxy)-2-cyclopenten-l-one (s). We also describe herein a novel synthesis of the key intermediates & and 42 in their optically active forms without chemical resolution. This totally asymmetric process constitutes an additional refinement of our approach to the synthesis of the prostaglandins.

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