Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Chambers C. Hughes; Dirk Trauner

doi:10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Chambers C. Hughes, Dirk Trauner

Chemistry

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

Abstract

Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

Original language	English (US)
Pages (from-to)	1569-1572
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	9
DOIs	https://doi.org/10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8
State	Published - May 3 2002

Keywords

Cyclization
Natural products
Palladium
Polycycles
Total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

Access to Document

10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

Cite this

@article{411d25cac862429fab0087e496cb845a,

title = "Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization",

abstract = "Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.",

keywords = "Cyclization, Natural products, Palladium, Polycycles, Total synthesis",

author = "Hughes, {Chambers C.} and Dirk Trauner",

year = "2002",

month = may,

day = "3",

doi = "10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8",

language = "English (US)",

volume = "41",

pages = "1569--1572",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "9",

}

TY - JOUR

T1 - Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

AU - Hughes, Chambers C.

AU - Trauner, Dirk

PY - 2002/5/3

Y1 - 2002/5/3

N2 - Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

AB - Sidestepping stereochemical inversion: In an expedient, asymmetric total synthesis of (-)-frondosin B a novel palladium-catalyzed cyclization establishes the tetracyclic skeleton (see scheme). The absolute stereochemistry of naturally occurring marine metabolite (+)-frondosin B, an interleukin-8 inhibitor, has been reassigned. Tf = trifluoromethanesulfonyl.

KW - Cyclization

KW - Natural products

KW - Palladium

KW - Polycycles

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=0037012743&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037012743&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

DO - 10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

M3 - Article

C2 - 19750668

AN - SCOPUS:0037012743

SN - 1433-7851

VL - 41

SP - 1569

EP - 1572

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

Concise total synthesis of (-)-frondosin B using a novel palladium-catalyzed cyclization

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this