Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 5, Pages 1775-1778Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo9027038
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Funding
- Spanish Ministry of Science and Technology [CTQ2005-06688-C02-01, CTQ2005-06688-C02-02]
- Conselleria de Educacion
- Ciencia y Empresa de la Generalitat Valenciana [ACOMP07/023]
- BANCAJA-UJI Foundation [PI-IB-2008-14]
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A stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A has been performed. The preparation of a cis-2,6-disubstituted tetrahydropyran ring via stereoselective reduction of an intermediate cyclic hemiacetal was one key feature of the synthesis. The macrocyclic lactone ring was created by means of a ring-closing metathesis (RCM), whereby the new C=C bond displayed exclusively the undesired Z configuration Conversion to the required E configuration was achieved via photochemical isomerization.
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