Total synthesis of (+)-lactiflorin by an intramolecular [2+2] photocycloaddition

Ping Lu; Thorsten Bach

doi:10.1002/anie.201106889

Total synthesis of (+)-lactiflorin by an intramolecular [2+2] photocycloaddition

Ping Lu
, Thorsten Bach

Chair of Organic Chemistry 1

Technical University of Munich

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

41 Scopus citations

Abstract

Enlightning synthesis: A light-induced intramolecular [2+2] photocycloaddition reaction (1→2) was the key step in the stereoselective synthesis of (+)-lactiflorin (3) and its triacetate. By comparison with reported analytical data, it was possible to unambiguously elucidate the structure of this natural product, to which three different structures had been previously assigned.

Original language	English
Pages (from-to)	1261-1264
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	5
DOIs	https://doi.org/10.1002/anie.201106889
State	Published - 27 Jan 2012

Keywords

cycloaddition
glycosylation
photochemistry
structure elucidation
total synthesis

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10.1002/anie.201106889

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abstract = "Enlightning synthesis: A light-induced intramolecular [2+2] photocycloaddition reaction (1→2) was the key step in the stereoselective synthesis of (+)-lactiflorin (3) and its triacetate. By comparison with reported analytical data, it was possible to unambiguously elucidate the structure of this natural product, to which three different structures had been previously assigned.",

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AU - Bach, Thorsten

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N2 - Enlightning synthesis: A light-induced intramolecular [2+2] photocycloaddition reaction (1→2) was the key step in the stereoselective synthesis of (+)-lactiflorin (3) and its triacetate. By comparison with reported analytical data, it was possible to unambiguously elucidate the structure of this natural product, to which three different structures had been previously assigned.

AB - Enlightning synthesis: A light-induced intramolecular [2+2] photocycloaddition reaction (1→2) was the key step in the stereoselective synthesis of (+)-lactiflorin (3) and its triacetate. By comparison with reported analytical data, it was possible to unambiguously elucidate the structure of this natural product, to which three different structures had been previously assigned.

KW - cycloaddition

KW - glycosylation

KW - photochemistry

KW - structure elucidation

KW - total synthesis

UR - https://www.scopus.com/pages/publications/84856195864

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JO - Angewandte Chemie - International Edition

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ER -

Total synthesis of (+)-lactiflorin by an intramolecular [2+2] photocycloaddition

Abstract

Keywords

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