Total synthesis and absolute stereochemical assignment of (+)- and (-)-galbulimima alkaloid 13 |
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Authors: | Movassaghi Mohammad Hunt Diana K Tjandra Meiliana |
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Institution: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. movassag@mit.edu |
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Abstract: | We describe the total synthesis of (+)- and (-)-galbulimima alkaloid 13. The absolute stereochemistry of natural (-)-galbulimima alkaloid 13 is revised to 2S. Sequential use of catalytic cross-coupling and cross-metathesis reactions followed by an intramolecular Diels-Alder reaction provided the required trans-decalin AB-ring system and masked the C16 carbonyl as an N-vinyl carbamate for late-stage unveiling in the form of the necessary C16 enone. A vinyl radical cyclization secured the C-ring, while successful execution of our strategy for introduction of the CDE-ring system in complex galbulimima alkaloids provided the target pentacycle with complete diastereoselection. |
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