Total synthesis and structural revision of callipeltoside C

Joseph Carpenter; Alan B. Northrup; De Michael Chung; John J.M. Wiener; Sung Gon Kim; David W.C. MacMillan

doi:10.1002/anie.200800086

Total synthesis and structural revision of callipeltoside C

Joseph Carpenter
, Alan B. Northrup
, De Michael Chung
, John J.M. Wiener
, Sung Gon Kim
, David W.C. MacMillan

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

85 Scopus citations

Abstract

(Chemical Equation Presented) Look again: Highlights of the 20-step synthesis of callipeltoside C include the proline-catalyzed direct aldol reaction, enantioselective α-oxyamination reaction, and rapid access to the carbohydrate framework using a de novo synthesis protocol. Based on this work the previously assigned absolute configuration of the pendent 2-O-methylevalose unit has been revised.

Original language	English (US)
Pages (from-to)	3568-3572
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	19
DOIs	https://doi.org/10.1002/anie.200800086
State	Published - Apr 28 2008

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Asymmetric synthesis
Callipeltoside C
Carbohydrates
Organocatalysis

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10.1002/anie.200800086

Cite this

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title = "Total synthesis and structural revision of callipeltoside C",

abstract = "(Chemical Equation Presented) Look again: Highlights of the 20-step synthesis of callipeltoside C include the proline-catalyzed direct aldol reaction, enantioselective α-oxyamination reaction, and rapid access to the carbohydrate framework using a de novo synthesis protocol. Based on this work the previously assigned absolute configuration of the pendent 2-O-methylevalose unit has been revised.",

keywords = "Asymmetric synthesis, Callipeltoside C, Carbohydrates, Organocatalysis",

author = "Joseph Carpenter and Northrup, \{Alan B.\} and Chung, \{De Michael\} and Wiener, \{John J.M.\} and Kim, \{Sung Gon\} and MacMillan, \{David W.C.\}",

year = "2008",

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doi = "10.1002/anie.200800086",

language = "English (US)",

volume = "47",

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AU - Carpenter, Joseph

AU - Northrup, Alan B.

AU - Chung, De Michael

AU - Wiener, John J.M.

AU - Kim, Sung Gon

AU - MacMillan, David W.C.

PY - 2008/4/28

Y1 - 2008/4/28

N2 - (Chemical Equation Presented) Look again: Highlights of the 20-step synthesis of callipeltoside C include the proline-catalyzed direct aldol reaction, enantioselective α-oxyamination reaction, and rapid access to the carbohydrate framework using a de novo synthesis protocol. Based on this work the previously assigned absolute configuration of the pendent 2-O-methylevalose unit has been revised.

AB - (Chemical Equation Presented) Look again: Highlights of the 20-step synthesis of callipeltoside C include the proline-catalyzed direct aldol reaction, enantioselective α-oxyamination reaction, and rapid access to the carbohydrate framework using a de novo synthesis protocol. Based on this work the previously assigned absolute configuration of the pendent 2-O-methylevalose unit has been revised.

KW - Asymmetric synthesis

KW - Callipeltoside C

KW - Carbohydrates

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/44049104472

UR - https://www.scopus.com/pages/publications/44049104472#tab=citedBy

U2 - 10.1002/anie.200800086

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AN - SCOPUS:44049104472

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SP - 3568

EP - 3572

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 19

ER -

Total synthesis and structural revision of callipeltoside C

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

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