Titanium-mediated fragment union processes in complex molecule synthesis

Development of a branched reaction pathway of high step economy for the synthesis of complex and diverse polyketides

Lark Perez, Glenn C. Micalizio

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

We describe a synthetic pathway to structurally complex and diverse polyketides based, in part, on regio- and stereoselective titanium-mediated coupling reactions. The sequences described allow for rapid assembly of polyketide-inspired architecture while providing significant flexibility for the establishment of diverse stereochemical relationships and substitution patterns along the carbon backbone (including stereodefined alkenes and 1,3-dienes, saturated and unsaturated lactones, hemiketals, α,β-unsaturated carbonyls, and spiroketals).

Original languageEnglish (US)
Pages (from-to)627-648
Number of pages22
JournalSynthesis
Issue number4
DOIs
StatePublished - Feb 15 2008
Externally publishedYes

Fingerprint

Polyketides
Titanium
Olefins
Substitution reactions
Molecules
Carbon
Alkenes
Lactones
spiroketal

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

@article{68e0dec7dcdb445dbda75a9fdbad798c,
title = "Titanium-mediated fragment union processes in complex molecule synthesis: Development of a branched reaction pathway of high step economy for the synthesis of complex and diverse polyketides",
abstract = "We describe a synthetic pathway to structurally complex and diverse polyketides based, in part, on regio- and stereoselective titanium-mediated coupling reactions. The sequences described allow for rapid assembly of polyketide-inspired architecture while providing significant flexibility for the establishment of diverse stereochemical relationships and substitution patterns along the carbon backbone (including stereodefined alkenes and 1,3-dienes, saturated and unsaturated lactones, hemiketals, α,β-unsaturated carbonyls, and spiroketals).",
author = "Lark Perez and Micalizio, {Glenn C.}",
year = "2008",
month = "2",
day = "15",
doi = "https://doi.org/10.1055/s-2008-1032160",
language = "English (US)",
pages = "627--648",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "4",

}

TY - JOUR

T1 - Titanium-mediated fragment union processes in complex molecule synthesis

T2 - Development of a branched reaction pathway of high step economy for the synthesis of complex and diverse polyketides

AU - Perez, Lark

AU - Micalizio, Glenn C.

PY - 2008/2/15

Y1 - 2008/2/15

N2 - We describe a synthetic pathway to structurally complex and diverse polyketides based, in part, on regio- and stereoselective titanium-mediated coupling reactions. The sequences described allow for rapid assembly of polyketide-inspired architecture while providing significant flexibility for the establishment of diverse stereochemical relationships and substitution patterns along the carbon backbone (including stereodefined alkenes and 1,3-dienes, saturated and unsaturated lactones, hemiketals, α,β-unsaturated carbonyls, and spiroketals).

AB - We describe a synthetic pathway to structurally complex and diverse polyketides based, in part, on regio- and stereoselective titanium-mediated coupling reactions. The sequences described allow for rapid assembly of polyketide-inspired architecture while providing significant flexibility for the establishment of diverse stereochemical relationships and substitution patterns along the carbon backbone (including stereodefined alkenes and 1,3-dienes, saturated and unsaturated lactones, hemiketals, α,β-unsaturated carbonyls, and spiroketals).

UR - http://www.scopus.com/inward/record.url?scp=39749093784&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=39749093784&partnerID=8YFLogxK

U2 - https://doi.org/10.1055/s-2008-1032160

DO - https://doi.org/10.1055/s-2008-1032160

M3 - Article

SP - 627

EP - 648

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 4

ER -