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First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product.
Org Biomol Chem. 2008 Oct 07; 6(19):3573-9.OB

Abstract

The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure beta-hydroxyallenes 12/13 to the corresponding dihydropyrans 14/15.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sawama Y
Organic Chemistry II, Dortmund University of Technology, D-44227, Dortmund, Germany.
Sawama Y
No affiliation info available
Krause N
No affiliation info available

MeSH

AlkadienesBiological ProductsCatalysisCyclizationGoldIsomerismSesquiterpenes

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19082158

Citation

Sawama, Yoshinari, et al. "First Total Synthesis of (R,R,R)- and (3R,5S,9R)-bejarol By Gold-catalyzed Allene Cycloisomerization and Determination of Absolute Configuration of the Natural Product." Organic & Biomolecular Chemistry, vol. 6, no. 19, 2008, pp. 3573-9.
Sawama Y, Sawama Y, Krause N. First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. Org Biomol Chem. 2008;6(19):3573-9.
Sawama, Y., Sawama, Y., & Krause, N. (2008). First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. Organic & Biomolecular Chemistry, 6(19), 3573-9. https://doi.org/10.1039/b807733a
Sawama Y, Sawama Y, Krause N. First Total Synthesis of (R,R,R)- and (3R,5S,9R)-bejarol By Gold-catalyzed Allene Cycloisomerization and Determination of Absolute Configuration of the Natural Product. Org Biomol Chem. 2008 Oct 7;6(19):3573-9. PubMed PMID: 19082158.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - First total synthesis of (R,R,R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. AU - Sawama,Yoshinari, AU - Sawama,Yuka, AU - Krause,Norbert, Y1 - 2008/07/11/ PY - 2008/12/17/entrez PY - 2008/12/17/pubmed PY - 2009/1/23/medline SP - 3573 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 6 IS - 19 N2 - The first total synthesis of (R,R,R)-bejarol and its (3R,5S,9R)-isomer has been accomplished which confirms the absolute configuration of the natural products. The key step is the gold-catalyzed cycloisomerization of the enantiomerically pure beta-hydroxyallenes 12/13 to the corresponding dihydropyrans 14/15. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/19082158/First_total_synthesis_of__RRR___and__3R5S9R__bejarol_by_gold_catalyzed_allene_cycloisomerization_and_determination_of_absolute_configuration_of_the_natural_product_ L2 - https://doi.org/10.1039/b807733a DB - PRIME DP - Unbound Medicine ER -