Avermectin–milbemycin synthetic studies. Part 7. An approach to the southern hemisphere of milbemycin α1
- 1 January 1992
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 979-989
- https://doi.org/10.1039/p19920000979
Abstract
An asymmetric approach to oxahydrindene 5, the southern hemisphere of the anthelmintic macrolide milbemycin α1, 2, is described. [2 + 2]-Photocycloaddition of the dihydrofuran chiral template (+)-11 with cyclobutenoate 12 furnished the requisite cis-anti-cis, head-to-tail photoadduct (+)-17 in 54% yield. de Mayo-type fragmentation then smoothly furnished hydrindane 21α,β; further elaboration afforded the 3,4-dihydro-4-normethyl southern fragment 39. Efforts to install the C(4) methyl group and C(3,4) unsaturation in several advanced intermediates related to 39 gave unsatisfactory results.Keywords
This publication has 82 references indexed in Scilit:
- Recent advances in avermectin researchPure and Applied Chemistry, 1990
- Avermectins and milbemycinsNatural Product Reports, 1986
- Ivermectin: A Potent New Antiparasitic AgentScience, 1983
- Milbemycins, a new family of macrolide antibiotics. Fermentation, isolation, physico-chemical properties and bioconversion of milbemycins J and K.The Journal of Antibiotics, 1983
- Milbemycins, a new family of macrolide antibiotics. Fermentation, isolation and physico-chemical properties of milbemycins D,E,F,G and H.The Journal of Antibiotics, 1983
- Milbemycins, a new family of macrolide antibiotics. Structure determination of milbemycins D,E,F,G,H,J and K.The Journal of Antibiotics, 1983
- Avermectins. Structure determinationJournal of the American Chemical Society, 1981
- Milbemycins, a new family of macrolide antibiotics: Fermentation, isolation and physico-chemical properties.The Journal of Antibiotics, 1980
- Avermectins, New Family of Potent Anthelmintic Agents: Isolation and Chromatographic PropertiesAntimicrobial Agents and Chemotherapy, 1979
- Structures of milbemycin β1, β2, and β3Tetrahedron Letters, 1975