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• W2010373553 endingPage "6032" @default.
• W2010373553 startingPage "6015" @default.
• W2010373553 abstract "Abstract The unique sesquiterpene punctaporonin C was synthesized starting from commercially available 7‐ tert ‐butoxynorbornadiene in a linear sequence of 29 steps and with an overall yield of 0.65 %. Key step of the synthesis was an intramolecular [2+2]‐photocycloaddition, in which the two vinylic double bonds in a 1,3‐divinyl‐2‐cyclopentyl tetronate were differentiated by reaction with the photoexcited tetronate. The reaction gave regio‐ and diastereoselective access to the tricyclic core skeleton of punctaporonin C in 63 % yield. Additional studies related to the tetronate [2+2]‐photocycloaddition revealed that even diastereotopic vinylic double bonds in a 1,3‐divinyl‐2‐cyclopentyl tetronate can be differentiated (d.r. up to 78:22). In the further course of the total synthesis the complete tetracyclic oxatetracyclo[6.3.2.0 1, 4 .0 5, 12 ]tridecane skeleton of punctaporonin C was established by an intramolecular aldol reaction, closing a seven‐membered oxepane ring. The nucleophilic methyl ketone employed in this step was generated by Wacker oxidation of the vinylic double bond, which was not involved in the [2+2]‐photocycloaddition. Several reactions employed in the synthetic sequence required adaptation to the rigid skeleton of punctaporonin C, for example, the reduction of a mesylate, the alkylation of a cyclobutane carboxylate, or the methyl addition to a prostereogenic carbonyl group." @default.
• W2010373553 created "2016-06-24" @default.
• W2010373553 creator A5013085430 @default.
• W2010373553 creator A5025015822 @default.
• W2010373553 date "2010-05-14" @default.
• W2010373553 modified "2023-10-18" @default.
• W2010373553 title "Total Synthesis of Punctaporonin C by a Regio- and Stereoselective [2+2]-Photocycloaddition" @default.
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• W2010373553 doi "https://doi.org/10.1002/chem.201000036" @default.
• W2010373553 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/20411543" @default.
• W2010373553 hasPublicationYear "2010" @default.
• W2010373553 type Work @default.
• W2010373553 sameAs 2010373553 @default.

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