Total Synthesis and Stereochemical Reassignment of (+)-Dolastatin 19

Ian Paterson; Alison D. Findlay; Gordon John Florence

doi:10.1021/ol060609q

Total Synthesis and Stereochemical Reassignment of (+)-Dolastatin 19

Ian Paterson, Alison D. Findlay, Gordon John Florence

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

Abstract

A revised configurational assignment for the cytotoxic marine macrolide dolastatin 19 is proposed and validated by total synthesis. Key features of the route include an asymmetric vinylogous aldol reaction to install the isolated C13 stereocenter and (E)-trisubstituted alkene, two sequential 1,4-syn boron-mediated aldol reactions, and a Mukaiyama glycosylation to append the L-rhamnose-derived pyranoside.

Original language	English
Pages (from-to)	2131-2134
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol060609q
Publication status	Published - 11 May 2006

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

MARINE NATURAL-PRODUCTS
HARE DOLABELLA-AURICULARIA
MACROLIDE
CALLIPELTOSIDE

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10.1021/ol060609q

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title = "Total Synthesis and Stereochemical Reassignment of (+)-Dolastatin 19",

abstract = "A revised configurational assignment for the cytotoxic marine macrolide dolastatin 19 is proposed and validated by total synthesis. Key features of the route include an asymmetric vinylogous aldol reaction to install the isolated C13 stereocenter and (E)-trisubstituted alkene, two sequential 1,4-syn boron-mediated aldol reactions, and a Mukaiyama glycosylation to append the L-rhamnose-derived pyranoside.",

keywords = "MARINE NATURAL-PRODUCTS, HARE DOLABELLA-AURICULARIA, MACROLIDE, CALLIPELTOSIDE",

author = "Ian Paterson and Findlay, \{Alison D.\} and Florence, \{Gordon John\}",

year = "2006",

month = may,

day = "11",

doi = "10.1021/ol060609q",

language = "English",

volume = "8",

pages = "2131--2134",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

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T1 - Total Synthesis and Stereochemical Reassignment of (+)-Dolastatin 19

AU - Paterson, Ian

AU - Findlay, Alison D.

AU - Florence, Gordon John

PY - 2006/5/11

Y1 - 2006/5/11

N2 - A revised configurational assignment for the cytotoxic marine macrolide dolastatin 19 is proposed and validated by total synthesis. Key features of the route include an asymmetric vinylogous aldol reaction to install the isolated C13 stereocenter and (E)-trisubstituted alkene, two sequential 1,4-syn boron-mediated aldol reactions, and a Mukaiyama glycosylation to append the L-rhamnose-derived pyranoside.

AB - A revised configurational assignment for the cytotoxic marine macrolide dolastatin 19 is proposed and validated by total synthesis. Key features of the route include an asymmetric vinylogous aldol reaction to install the isolated C13 stereocenter and (E)-trisubstituted alkene, two sequential 1,4-syn boron-mediated aldol reactions, and a Mukaiyama glycosylation to append the L-rhamnose-derived pyranoside.

KW - MARINE NATURAL-PRODUCTS

KW - HARE DOLABELLA-AURICULARIA

KW - MACROLIDE

KW - CALLIPELTOSIDE

UR - https://www.scopus.com/pages/publications/33744723813

UR - http://pubs3.acs.org/acs/journals/doilookup?in_doi=10.1021/ol060609q

U2 - 10.1021/ol060609q

DO - 10.1021/ol060609q

M3 - Article

SN - 1523-7060

VL - 8

SP - 2131

EP - 2134

JO - Organic Letters

JF - Organic Letters

IS - 10

ER -

Total Synthesis and Stereochemical Reassignment of (+)-Dolastatin 19

Abstract

UN SDGs

Keywords

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