Asperidine B: Total synthesis and structure correction

Lachlan J.N. Waddell; Olivia F.B. Watts; Praphatsorn Saetang; Vatcharin Rukachaisirikul; Roderick W. Bates

doi:10.1016/j.tetlet.2020.152078

Asperidine B: Total synthesis and structure correction

Lachlan J.N. Waddell, Olivia F.B. Watts, Praphatsorn Saetang, Vatcharin Rukachaisirikul^*, Roderick W. Bates

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement with that of the natural product, the structure of asperidine B is reassigned as (+)-preussin.

Original language	English
Article number	152078
Journal	Tetrahedron Letters
Volume	61
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2020.152078
Publication status	Published - Jul 2 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Elsevier Ltd

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Benzylation
Hydroformylation
Piperidine
Pyrrolidine
Synthesis

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10.1016/j.tetlet.2020.152078

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title = "Asperidine B: Total synthesis and structure correction",

abstract = "A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement with that of the natural product, the structure of asperidine B is reassigned as (+)-preussin.",

keywords = "Benzylation, Hydroformylation, Piperidine, Pyrrolidine, Synthesis",

author = "Waddell, \{Lachlan J.N.\} and Watts, \{Olivia F.B.\} and Praphatsorn Saetang and Vatcharin Rukachaisirikul and Bates, \{Roderick W.\}",

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day = "2",

doi = "10.1016/j.tetlet.2020.152078",

language = "English",

volume = "61",

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T2 - Total synthesis and structure correction

AU - Waddell, Lachlan J.N.

AU - Watts, Olivia F.B.

AU - Saetang, Praphatsorn

AU - Rukachaisirikul, Vatcharin

AU - Bates, Roderick W.

PY - 2020/7/2

Y1 - 2020/7/2

N2 - A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement with that of the natural product, the structure of asperidine B is reassigned as (+)-preussin.

AB - A synthesis of the proposed structure of asperidine B is reported, involving a tandem hydroformylation-condensation reaction, a diastereoselective dihydroxylation and the addition of an organozinc reagent to an iminium ion. As the spectroscopic data for the synthetic material is not in agreement with that of the natural product, the structure of asperidine B is reassigned as (+)-preussin.

KW - Benzylation

KW - Hydroformylation

KW - Piperidine

KW - Pyrrolidine

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=85085753723&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85085753723&partnerID=8YFLogxK

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DO - 10.1016/j.tetlet.2020.152078

M3 - Article

AN - SCOPUS:85085753723

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

M1 - 152078

ER -

Asperidine B: Total synthesis and structure correction

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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