Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin

K. C. Nicolaou; Xuefeng Jiang; Peter J. Lindsay-Scott; Andrei Corbu; Sawako Yamashiro; Andrea Bacconi; Velia M. Fowler

doi:10.1002/anie.201006780

Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin

K. C. Nicolaou, Xuefeng Jiang, Peter J. Lindsay-Scott, Andrei Corbu, Sawako Yamashiro, Andrea Bacconi, Velia M. Fowler

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

47 Citations (Scopus)

Abstract

Convergence and a biological dichotomy! Monorhizopodin (see structure) and its C16 epimer have been synthesized through a highly convergent strategy. Unlike the antitumor agent rhizopodin which is their naturally occurring dimer, monorhizopodin and its epimer exhibit potent inhibition of actin polymerization but no significant cytotoxicity.

Original language	English
Pages (from-to)	1139-1144
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	5
DOIs	https://doi.org/10.1002/anie.201006780
Publication status	Published - 2011 Feb 1

Keywords

macrolactonization
natural products
polyketides
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.201006780

Fingerprint Dive into the research topics of 'Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin'. Together they form a unique fingerprint.

Cite this

Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin. / Nicolaou, K. C.; Jiang, Xuefeng; Lindsay-Scott, Peter J.; Corbu, Andrei; Yamashiro, Sawako; Bacconi, Andrea; Fowler, Velia M.

In: Angewandte Chemie - International Edition, Vol. 50, No. 5, 01.02.2011, p. 1139-1144.

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

@article{453d60d6d8d3466bb1c55c6a8dc0d588,

title = "Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin",

abstract = "Convergence and a biological dichotomy! Monorhizopodin (see structure) and its C16 epimer have been synthesized through a highly convergent strategy. Unlike the antitumor agent rhizopodin which is their naturally occurring dimer, monorhizopodin and its epimer exhibit potent inhibition of actin polymerization but no significant cytotoxicity.",

keywords = "macrolactonization, natural products, polyketides, total synthesis",

author = "Nicolaou, {K. C.} and Xuefeng Jiang and Lindsay-Scott, {Peter J.} and Andrei Corbu and Sawako Yamashiro and Andrea Bacconi and Fowler, {Velia M.}",

year = "2011",

month = feb,

day = "1",

doi = "10.1002/anie.201006780",

language = "English",

volume = "50",

pages = "1139--1144",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "5",

}

TY - JOUR

T1 - Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin

AU - Nicolaou, K. C.

AU - Jiang, Xuefeng

AU - Lindsay-Scott, Peter J.

AU - Corbu, Andrei

AU - Yamashiro, Sawako

AU - Bacconi, Andrea

AU - Fowler, Velia M.

PY - 2011/2/1

Y1 - 2011/2/1

N2 - Convergence and a biological dichotomy! Monorhizopodin (see structure) and its C16 epimer have been synthesized through a highly convergent strategy. Unlike the antitumor agent rhizopodin which is their naturally occurring dimer, monorhizopodin and its epimer exhibit potent inhibition of actin polymerization but no significant cytotoxicity.

AB - Convergence and a biological dichotomy! Monorhizopodin (see structure) and its C16 epimer have been synthesized through a highly convergent strategy. Unlike the antitumor agent rhizopodin which is their naturally occurring dimer, monorhizopodin and its epimer exhibit potent inhibition of actin polymerization but no significant cytotoxicity.

KW - macrolactonization

KW - natural products

KW - polyketides

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=79251562197&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79251562197&partnerID=8YFLogxK

U2 - 10.1002/anie.201006780

DO - 10.1002/anie.201006780

M3 - Article

C2 - 21268213

AN - SCOPUS:79251562197

VL - 50

SP - 1139

EP - 1144

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 5

ER -