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Total Synthesis of Palodesangrens A and C.
Tangdenpaisal, Kassrin; Songthammawat, Poramate; Ruchirawat, Somsak; Ploypradith, Poonsakdi.
Affiliation
  • Tangdenpaisal K; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
  • Songthammawat P; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
  • Ruchirawat S; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
  • Ploypradith P; Program in Chemical Sciences, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, 906 Kamphaeng Phet 6 Road, Laksi, Bangkok 10210, Thailand.
J Org Chem ; 87(1): 386-398, 2022 01 07.
Article in En | MEDLINE | ID: mdl-34904441
ABSTRACT
Palodesangrens A and C along with the common tetracyclic core are prepared from simple benzaldehyde and acetophenone derivatives in a 10-step longest linear sequence which featured the Diels-Alder reaction forming the cyclohexene moiety, LiAlH4 isomerization, stereoselective acid-catalyzed cyclization forming the chroman moiety, regioselective iodination/vinyl Suzuki cross-coupling reaction, and ring-closing metathesis (RCM) forming the 2H-pyran-2-one. Overall, the desired palodesangrens A and C are obtained in 6.1% and 6.4% yields, respectively.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Pyrans Language: En Journal: J Org Chem Year: 2022 Document type: Article Affiliation country: Thailand
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Pyrans Language: En Journal: J Org Chem Year: 2022 Document type: Article Affiliation country: Thailand