Syntheses of the AB and EFGH ring segments of gambierol

Isao Kadota, Chie Kadowaki, Choul Hong Park, Hiroyoshi Takamura, Kumi Sato, Philip W.H. Chan, Stephan Thorand, Yoshinori Yamamoto

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Abstract

Stereocontrolled syntheses of the AB and EFGH ring systems of gambierol (1) are described. The two key intermediates 3 and 55, representing the AB and EFGH ring frameworks, were prepared from 2-deoxy-D-ribose via linear sequences. Brown's asymmetric allylboration and the intramolecular hetero-Michael reaction were successfully applied to the construction of the A ring moiety. Synthesis of the EFGH ring segment 55 was achieved by the SmI2 mediated reductive cyclization, constructing the EF ring bearing two 1,3-diaxial methyl groups, and the palladium catalyzed coupling of enol triflate and zinc bishomoenolate, making the GH ring moiety. Attempted convergent approaches toward the EFGH ring framework are also described.

Original languageEnglish
Pages (from-to)1799-1816
Number of pages18
JournalTetrahedron
Volume58
Issue number10
DOIs
Publication statusPublished - 4 Mar 2002
Externally publishedYes

Keywords

  • AB and EFGH ring segments
  • Gambierol
  • Polycyclic ether
  • Stereocontrolled synthesis

Cite this

Kadota, I., Kadowaki, C., Park, C. H., Takamura, H., Sato, K., Chan, P. W. H., Thorand, S., & Yamamoto, Y. (2002). Syntheses of the AB and EFGH ring segments of gambierol. Tetrahedron, 58(10), 1799-1816. https://doi.org/10.1016/S0040-4020(02)00039-X