Enantioselective [4 + 2]-Annulation of Chiral Crotylsilanes: Application to the Synthesis of a C1−C22 Fragment of Leucascandrolide A

descriptionPublicationkeyboard_double_arrow_right Article 19 Sep 2003 English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 5, pages 3,995-3,998 (issn: 1523-7060, eissn: 1523-7052,

Copyright policy )

Authors: Les A, Dakin; James S, Panek;

doi: 10.1021/ol035581m

pmid: 14535762

Enantioselective [4 + 2]-Annulation of Chiral Crotylsilanes: Application to the Synthesis of a C1−C22 Fragment of Leucascandrolide A

- Summary
- Subjects
- Related research
  (5)
- Metrics

Abstract

[reaction: see text] The asymmetric synthesis of a C1-C22 fragment (2) of leucascandrolide A is described. Synthetic highlights include the construction of the C9-C22 pyran fragment using a formal [4 + 2]-annulation of a chiral organosilane. A diastereoselctive Mukaiyama aldol was used to introduce the C9 stereocenter and complete the assembly of the macrocycle's carbon skeleton.

Related Organizations

Boston College
United States
Boston University
United States

Keywords

Models, Chemical, Stereoisomerism, Sesquiterpenes

5 Research products, page 1 of 1

Mukaiyama Aldol−Prins Cyclization Cascade Reaction: A Formal Total Synthesis of Leucascandrolide A
2001IsAmongTopNSimilarDocuments
ChemInform Abstract: Synthetic Efforts Toward the Macrolactone Core (I) of Leucascandrolide A (II).
2008IsAmongTopNSimilarDocuments
Total Synthesis of Leucascandrolide A
2002IsAmongTopNSimilarDocuments
Synthesis of the C_1‘−C_11‘Segment of Leucascandrolide A
2001IsAmongTopNSimilarDocuments
Total Synthesis of Leucascandrolide A: A New Application of the Mukaiyama Aldol−Prins Reaction
2007IsAmongTopNSimilarDocuments

Impact byBIP!

	selected citations These citations are derived from selected sources. This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	21
	popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.	Average
	influence This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	Top 10%
	impulse This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.	Top 10%

Found an issue? Give us feedback

21

Average

Top 10%

Fields of Science

Fields of Science

Upload OA version

Are you the author of this publication? Upload your Open Access version to Zenodo!

It’s fast and easy, just two clicks!

uploadUpload now

Enantioselective [4 + 2]-Annulation of Chiral Crotylsilanes: Application to the Synthesis of a C1−C22 Fragment of Leucascandrolide A

Enantioselective [4 + 2]-Annulation of Chiral Crotylsilanes: Application to the Synthesis of a C1−C22 Fragment of Leucascandrolide A

5 Research products, page 1 of 1

Mukaiyama Aldol−Prins Cyclization Cascade Reaction: A Formal Total Synthesis of Leucascandrolide A

ChemInform Abstract: Synthetic Efforts Toward the Macrolactone Core (I) of Leucascandrolide A (II).

Total Synthesis of Leucascandrolide A

Synthesis of the C1‘−C11‘Segment of Leucascandrolide A

Total Synthesis of Leucascandrolide A: A New Application of the Mukaiyama Aldol−Prins Reaction

Synthesis of the C_1‘−C_11‘Segment of Leucascandrolide A