An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

Ke Kong; John A. Enquist; Monica E. McCallum; Genessa M. Smith; Takanori Matsumaru; Elnaz Menhaji-Klotz; John L. Wood

doi:10.1021/ja405548b

An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

Ke Kong, John A. Enquist, Monica E. McCallum, Genessa M. Smith, Takanori Matsumaru, Elnaz Menhaji-Klotz, John L. Wood

Research output: Contribution to journal › Article › peer-review

65 Citations (Scopus)

Abstract

This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

Original language	English
Pages (from-to)	10890-10893
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	30
DOIs	https://doi.org/10.1021/ja405548b
Publication status	Published - 2013 Jul 31
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja405548b

Cite this

@article{dccfbefd66d24ea2928e8e7b13071c1a,

title = "An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B",

abstract = "This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.",

author = "Ke Kong and Enquist, {John A.} and McCallum, {Monica E.} and Smith, {Genessa M.} and Takanori Matsumaru and Elnaz Menhaji-Klotz and Wood, {John L.}",

year = "2013",

month = jul,

day = "31",

doi = "10.1021/ja405548b",

language = "English",

volume = "135",

pages = "10890--10893",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "30",

}

TY - JOUR

T1 - An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

AU - Kong, Ke

AU - Enquist, John A.

AU - McCallum, Monica E.

AU - Smith, Genessa M.

AU - Matsumaru, Takanori

AU - Menhaji-Klotz, Elnaz

AU - Wood, John L.

PY - 2013/7/31

Y1 - 2013/7/31

N2 - This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

AB - This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

UR - http://www.scopus.com/inward/record.url?scp=84881041928&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84881041928&partnerID=8YFLogxK

U2 - 10.1021/ja405548b

DO - 10.1021/ja405548b

M3 - Article

C2 - 23837485

AN - SCOPUS:84881041928

VL - 135

SP - 10890

EP - 10893

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 30

ER -

An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this