A stereocontrolled construction of the side chain of brassinclide and homobrassinolide has been achieved via the tandem vicinal dialkylation of the pyranone moiety as a key step.
Homobrassinolide (2) and (22S, 23S)-22,23-epi-homobrassinolide (4) were synthesized fromstigmasterol in seven steps respectively in 4.7% and 24.1% overall yields. The ratio of 2 to 4is 1:5. The key step is the highly ...Homobrassinolide (2) and (22S, 23S)-22,23-epi-homobrassinolide (4) were synthesized fromstigmasterol in seven steps respectively in 4.7% and 24.1% overall yields. The ratio of 2 to 4is 1:5. The key step is the highly regioselective formation of the B--homo-7-oxa-lactone ringby oxidation of an enol silyl ether with 3--chloro-peroxybenzoic acid.展开更多
文摘A stereocontrolled construction of the side chain of brassinclide and homobrassinolide has been achieved via the tandem vicinal dialkylation of the pyranone moiety as a key step.
文摘Homobrassinolide (2) and (22S, 23S)-22,23-epi-homobrassinolide (4) were synthesized fromstigmasterol in seven steps respectively in 4.7% and 24.1% overall yields. The ratio of 2 to 4is 1:5. The key step is the highly regioselective formation of the B--homo-7-oxa-lactone ringby oxidation of an enol silyl ether with 3--chloro-peroxybenzoic acid.
