Synthesis of novel C2-C3′N-linked macrocyclic taxoids by means of highly regioselective heck macrocyclization

Xudong Geng; Michael L. Miller; Songnian Lin; Iwao Ojima

doi:10.1021/ol0354627

Synthesis of novel C2-C3′N-linked macrocyclic taxoids by means of highly regioselective heck macrocyclization

Xudong Geng
, Michael L. Miller
, Songnian Lin
, Iwao Ojima

Chemistry

Stony Brook University

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

60 Scopus citations

Abstract

(Matrix presented) Novel C2-C3′N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3′N give exo-products exclusively. However, the endo-products are formed with up to 100% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic.

Original language	English
Pages (from-to)	3733-3736
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	20
DOIs	https://doi.org/10.1021/ol0354627
State	Published - Oct 2 2003

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title = "Synthesis of novel C2-C3′N-linked macrocyclic taxoids by means of highly regioselective heck macrocyclization",

abstract = "(Matrix presented) Novel C2-C3′N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3′N give exo-products exclusively. However, the endo-products are formed with up to 100\% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic.",

author = "Xudong Geng and Miller, \{Michael L.\} and Songnian Lin and Iwao Ojima",

year = "2003",

month = oct,

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doi = "10.1021/ol0354627",

language = "English",

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pages = "3733--3736",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Synthesis of novel C2-C3′N-linked macrocyclic taxoids by means of highly regioselective heck macrocyclization

AU - Geng, Xudong

AU - Miller, Michael L.

AU - Lin, Songnian

AU - Ojima, Iwao

PY - 2003/10/2

Y1 - 2003/10/2

N2 - (Matrix presented) Novel C2-C3′N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3′N give exo-products exclusively. However, the endo-products are formed with up to 100% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic.

AB - (Matrix presented) Novel C2-C3′N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3′N give exo-products exclusively. However, the endo-products are formed with up to 100% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic.

UR - https://www.scopus.com/pages/publications/0142074816

U2 - 10.1021/ol0354627

DO - 10.1021/ol0354627

M3 - Article

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Synthesis of novel C2-C3′N-linked macrocyclic taxoids by means of highly regioselective heck macrocyclization

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