Enantioselective construction of the tricyclic core of curcusones A-D a cross-electrophile coupling approach
Herein we report our recent progress toward the enantioselective total synthesis of the diterpenoid natural products curcusones A-D by means of complementary Stetter annulation or ring-closing metathesis (RCM) disconnections. Using the latter approach, we have achieved the concise construction of th...
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| Published in | Chemical science (Cambridge) Vol. 1; no. 45; pp. 1562 - 1565 |
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| Main Authors | , |
| Format | Journal Article |
| Published |
20.11.2019
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| Online Access | Get full text |
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| Abstract | Herein we report our recent progress toward the enantioselective total synthesis of the diterpenoid natural products curcusones A-D by means of complementary Stetter annulation or ring-closing metathesis (RCM) disconnections. Using the latter approach, we have achieved the concise construction of the
5-7-6
carbocyclic core embedded in each member of the curcusone family. Essential to this route is the use of a cross-electrophile coupling strategy, which has not previously been harnessed in the context of natural product synthesis.
Rapid assembly of the carbocyclic core of the curcusone family of natural products is achieved using reductive cross coupling and ring-closing metathesis disconnections. |
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| AbstractList | Herein we report our recent progress toward the enantioselective total synthesis of the diterpenoid natural products curcusones A-D by means of complementary Stetter annulation or ring-closing metathesis (RCM) disconnections. Using the latter approach, we have achieved the concise construction of the
5-7-6
carbocyclic core embedded in each member of the curcusone family. Essential to this route is the use of a cross-electrophile coupling strategy, which has not previously been harnessed in the context of natural product synthesis.
Rapid assembly of the carbocyclic core of the curcusone family of natural products is achieved using reductive cross coupling and ring-closing metathesis disconnections. |
| Author | Wright, Austin C Stoltz, Brian M |
| AuthorAffiliation | California Institute of Technology Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering Division of Chemistry and Chemical Engineering |
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| ContentType | Journal Article |
| DOI | 10.1039/c9sc04127c |
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| Notes | For ESI and crystallographic data in CIF or other electronic format see DOI 10.1039/c9sc04127c Electronic supplementary information (ESI) available: Experimental procedures, NMR and IR spectra, and X-ray crystallography data. CCDC 1955394 |
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| Title | Enantioselective construction of the tricyclic core of curcusones A-D a cross-electrophile coupling approach |
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