Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L

A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels–Alder (HDA) reaction, a Suzuki–Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 18; no. 21; pp. 2606 - 2612
Main Authors Washio, Takuya, Nambu, Hisanori, Anada, Masahiro, Hashimoto, Shunichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 22.10.2007
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ORGANOBORON COMPOUNDS
SEEDS
COUPLING REACTIONS
ANTIPROLIFERATIVE DIARYLHEPTANOIDS
BLEPHAROCALYXINS C-E
ALPINIA-BLEPHAROCALYX
EPICALYXIN-F
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Summary:A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels–Alder (HDA) reaction, a Suzuki–Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis[( R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh 2( R-BPTPI) 4, provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2007.10.025