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Synthesis of indenol- and azulenol derivatives via platinum dichloride-catalyzed intramolecular hydroxy- or alkoxycyclization of cyclic dienynes.
J Org Chem. 2008 Apr 04; 73(7):2902-4.JO

Abstract

Platinum dichloride-catalyzed hydroxy- or alkoxycyclization of cyclohexadienynes gives indenol derivatives, whereas hydroxy- or alkoxycyclization of cycloheptadienynes produces azulenol derivatives. The cyclization reaction proceeds via a cyclopropyl platinacarbene intermediate and allows for the direct stereocontrol of three contiguous stereogenic centers of the fused bicyclic skeletons. The transient reactive intermediate obtained from PtCl2-catalyzed cyclization reaction of a cyclohexadienyndiol can be trapped intramolecularly by a hydroxyl group to afford an oxatricyclo[5.4.0.04,8]undecane ring skeleton with extreme diastereoselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yeh MC
Department of Chemistry, National Taiwan Normal University, 88 Ding-Jou Road, Section 4, Taipei 11677, Taiwan, Republic of China. cheyeh@scc.ntnu.edu.tw
Tsao WC
No affiliation info available
Cheng ST
No affiliation info available

MeSH

AlkynesAzulenesCatalysisCyclizationHydroxyl RadicalIndenesMolecular StructurePlatinum CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

18331053

Citation

Yeh, Ming-Chang P., et al. "Synthesis of Indenol- and Azulenol Derivatives Via Platinum Dichloride-catalyzed Intramolecular Hydroxy- or Alkoxycyclization of Cyclic Dienynes." The Journal of Organic Chemistry, vol. 73, no. 7, 2008, pp. 2902-4.
Yeh MC, Tsao WC, Cheng ST. Synthesis of indenol- and azulenol derivatives via platinum dichloride-catalyzed intramolecular hydroxy- or alkoxycyclization of cyclic dienynes. J Org Chem. 2008;73(7):2902-4.
Yeh, M. C., Tsao, W. C., & Cheng, S. T. (2008). Synthesis of indenol- and azulenol derivatives via platinum dichloride-catalyzed intramolecular hydroxy- or alkoxycyclization of cyclic dienynes. The Journal of Organic Chemistry, 73(7), 2902-4. https://doi.org/10.1021/jo702424w
Yeh MC, Tsao WC, Cheng ST. Synthesis of Indenol- and Azulenol Derivatives Via Platinum Dichloride-catalyzed Intramolecular Hydroxy- or Alkoxycyclization of Cyclic Dienynes. J Org Chem. 2008 Apr 4;73(7):2902-4. PubMed PMID: 18331053.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of indenol- and azulenol derivatives via platinum dichloride-catalyzed intramolecular hydroxy- or alkoxycyclization of cyclic dienynes. AU - Yeh,Ming-Chang P, AU - Tsao,Wen-Cheng, AU - Cheng,Sau-Tin, Y1 - 2008/03/11/ PY - 2008/3/12/pubmed PY - 2008/6/20/medline PY - 2008/3/12/entrez SP - 2902 EP - 4 JF - The Journal of organic chemistry JO - J Org Chem VL - 73 IS - 7 N2 - Platinum dichloride-catalyzed hydroxy- or alkoxycyclization of cyclohexadienynes gives indenol derivatives, whereas hydroxy- or alkoxycyclization of cycloheptadienynes produces azulenol derivatives. The cyclization reaction proceeds via a cyclopropyl platinacarbene intermediate and allows for the direct stereocontrol of three contiguous stereogenic centers of the fused bicyclic skeletons. The transient reactive intermediate obtained from PtCl2-catalyzed cyclization reaction of a cyclohexadienyndiol can be trapped intramolecularly by a hydroxyl group to afford an oxatricyclo[5.4.0.04,8]undecane ring skeleton with extreme diastereoselectivity. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/18331053/Synthesis_of_indenol__and_azulenol_derivatives_via_platinum_dichloride_catalyzed_intramolecular_hydroxy__or_alkoxycyclization_of_cyclic_dienynes_ DB - PRIME DP - Unbound Medicine ER -