Journal of Organic Chemistry p. 6229 - 6234 (1993)
Update date:2022-08-03
Topics:
Marshall, James A.
Luke, George P.
The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide.The key step entailed MgBr2-promoted addition of the (S)-γ-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether.The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.
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