Asymmetric Total Synthesis of Lepadiformine C Using Memory of Chirality in an Intramolecular Ester Enolate Michael Addition

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초록

The asymmetric synthesis of lepadiformine C was achieved using D-proline as the only chiral source. The synthetic strategy features the use of the principle of "memory of chirality" in an intramolecular Michael addition to construct the bicyclic intermediate without the aid of external chiral sources. A brief mechanistic rationale is presented to account for the stereochemical outcome.

키워드

TRICYCLIC MARINE ALKALOIDS; AMINO-ACID DERIVATIVES; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; RING-SYSTEM; QUATERNARY; (-)-LEPADIFORMINE; (-)-FASICULARIN; FASICULARIN; ALKYLATION
제목
Asymmetric Total Synthesis of Lepadiformine C Using Memory of Chirality in an Intramolecular Ester Enolate Michael Addition
저자
Lee, Seokwoo; Bae, Minsik; In, Jinkyung; Kim, Jae Hyun; Kim, Sanghee
DOI
10.1021/acs.orglett.6b03550
발행일
2017-01
유형
Article
저널명
Organic Letters
권
19
호
1
페이지
254 ~ 257