The 3,4-dihydro-2H-pyran approach to (+)-milbemycin β3. Part 2. An improved synthesis of (2R,4S,6S,8R,9S)-2-[(5R)-(2E)-3-methyl-5-formyl-hex-2-en-1-yl]-8,9-dimethyl-4-(dimethyl-t-butylsilyloxy)-1,7-dioxaspiro[5.5]undecane
- 31 December 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2189-2194
- https://doi.org/10.1039/p19870002189
Abstract
A more efficient synthesis of the title compound (2), previously used in a total synthesis of (+)-milbemycin β3(1), is described. The key step in the sequence involves a nucleophilic cleavage of the oxirane (4) by the organocuprate derived from metallation of (2R,3S)-2,3-dimethyl-3,4-dihydro-2H-pyran (5).This publication has 6 references indexed in Scilit:
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