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Org Lett. 2013 Feb 15;15(4):812-5. doi: 10.1021/ol400038h. Epub 2013 Jan 31.

Asymmetric total syntheses of ansamacrolactams (+)-Q-1047H-A-A and (+)-Q-1047H-R-A.

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1
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.

Abstract

The total syntheses of ansamacrolactams (+)-Q-1047H-A-A (16) and (+)-Q-1047H-R-A (17) have been achieved for the first time in 17 steps, leading to the reassignment of the relative stereochemistries and absolute configurations of their natural counterparts. The key steps in the synthetic work included an asymmetric chelation-controlled vinylogous Mukaiyama aldol reaction for the stereoselective synthesis of the syn-aldol adduct 7b and an intramolecular SmI(2)-mediated Reformatsky reaction for the formation of the macrocyclic lactam 14.

PMID:
23368957
DOI:
10.1021/ol400038h
[Indexed for MEDLINE]
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