An Efficient Synthesis of (±)-Dehaloperophoramidine

Research output: Contribution to journalArticle

Standard

An Efficient Synthesis of (±)-Dehaloperophoramidine. / Hoang, Anita; Popov, Kirill; Somfai, Peter.

In: Journal of Organic Chemistry, Vol. 82, No. 4, 17.02.2017, p. 2171-2176.

Research output: Contribution to journalArticle

Harvard

APA

CBE

MLA

Vancouver

Author

Hoang, Anita ; Popov, Kirill ; Somfai, Peter. / An Efficient Synthesis of (±)-Dehaloperophoramidine. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 4. pp. 2171-2176.

RIS

TY - JOUR

T1 - An Efficient Synthesis of (±)-Dehaloperophoramidine

AU - Hoang, Anita

AU - Popov, Kirill

AU - Somfai, Peter

PY - 2017/2/17

Y1 - 2017/2/17

N2 - Perophoramidine and communesin F are structurally related indole alkaloids with an intriguing polycyclic core containing vicinal all-carbon quaternary stereocenters. Dehaloperophoramidine is a dehalogenated synthetic analogue of perophoramidine. Synthetic studies toward the total synthesis of dehaloperophoramidine have led to the discovery of two novel domino processes, the first encompassing four steps and resulting in the formation of an ortho-amide. A thorough study of the reactivity of the ortho-amide functionality revealed the second domino reaction and ultimately yielded the target molecule. The vicinal all-carbon quaternary stereocenters having trans relative stereochemistry are constructed early in the reaction sequence by employing Overman's samarium mediated reductive dialkylation procedure. Described are the synthetic studies that led to the final eight-step synthesis of dehaloperophoramidine.

AB - Perophoramidine and communesin F are structurally related indole alkaloids with an intriguing polycyclic core containing vicinal all-carbon quaternary stereocenters. Dehaloperophoramidine is a dehalogenated synthetic analogue of perophoramidine. Synthetic studies toward the total synthesis of dehaloperophoramidine have led to the discovery of two novel domino processes, the first encompassing four steps and resulting in the formation of an ortho-amide. A thorough study of the reactivity of the ortho-amide functionality revealed the second domino reaction and ultimately yielded the target molecule. The vicinal all-carbon quaternary stereocenters having trans relative stereochemistry are constructed early in the reaction sequence by employing Overman's samarium mediated reductive dialkylation procedure. Described are the synthetic studies that led to the final eight-step synthesis of dehaloperophoramidine.

UR - http://www.scopus.com/inward/record.url?scp=85013214695&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b02969

DO - 10.1021/acs.joc.6b02969

M3 - Article

VL - 82

SP - 2171

EP - 2176

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 1520-6904

IS - 4

ER -