Divergent Total Syntheses of Phragmalin and Khayanolide-Type Limonoids: A Torquoselective Interrupted Nazarov
Peirong Rao1,2, Dongmin Tang2, Qidong Xia1
1Department of Chemistry, Zhejiang University, Hangzhou 310058, China.
Abstract:
The asymmetric and divergent total syntheses of two phragmalin (moluccensins G and H) and two khayanolide-type (krishnolide F and khayseneganin F) limonoids were disclosed, which employed a torquoselective interrupted Nazarov cyclization as the key step. Taken together with a Liebeskind-Srogl coupling, a benzoin condensation, and bidirectional acyloin rearrangements, our strategy would simplify the synthetic design of both phragmalin and khayanolide-type limonoids and facilitate their modular syntheses. Moreover, the described approach also provides additional insights into the biosynthetic relationships between these two distinct skeletons.
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