Concise synthesis of capuramycin

Michio Kurosu, Kai Li, Dean C. Crick

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with <30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.

Original languageEnglish (US)
Pages (from-to)2393-2396
Number of pages4
JournalOrganic letters
Volume11
Issue number11
DOIs
StatePublished - Jun 4 2009
Externally publishedYes

Fingerprint

synthesis
drugs
Pharmacokinetics
Uridine
analogs
Derivatives
Pharmaceutical Preparations
capuramycin
cyanohydrin
Lead

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Concise synthesis of capuramycin. / Kurosu, Michio; Li, Kai; Crick, Dean C.

In: Organic letters, Vol. 11, No. 11, 04.06.2009, p. 2393-2396.

Research output: Contribution to journalArticle

Kurosu, M, Li, K & Crick, DC 2009, 'Concise synthesis of capuramycin', Organic letters, vol. 11, no. 11, pp. 2393-2396. https://doi.org/10.1021/ol900458w
Kurosu, Michio ; Li, Kai ; Crick, Dean C. / Concise synthesis of capuramycin. In: Organic letters. 2009 ; Vol. 11, No. 11. pp. 2393-2396.
@article{eca3eba61d5e417ca079c0bc4ae16c2c,
title = "Concise synthesis of capuramycin",
abstract = "A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with <30{\%} overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.",
author = "Michio Kurosu and Kai Li and Crick, {Dean C.}",
year = "2009",
month = "6",
day = "4",
doi = "10.1021/ol900458w",
language = "English (US)",
volume = "11",
pages = "2393--2396",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "11",

}

TY - JOUR

T1 - Concise synthesis of capuramycin

AU - Kurosu, Michio

AU - Li, Kai

AU - Crick, Dean C.

PY - 2009/6/4

Y1 - 2009/6/4

N2 - A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with <30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.

AB - A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with <30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.

UR - http://www.scopus.com/inward/record.url?scp=66149190559&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=66149190559&partnerID=8YFLogxK

U2 - 10.1021/ol900458w

DO - 10.1021/ol900458w

M3 - Article

VL - 11

SP - 2393

EP - 2396

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 11

ER -