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Synfacts 2017; 13(03): 0227
DOI: 10.1055/s-0036-1589995
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Syntheses of Sarcandrolide J and Shizukaol D

Contributor(s):
Erick M. Carreira
,
Nicole Hauser
Du B. Deng H. Man Y. Liu B. * Sichuan University and China Pharmaceutical University, Nanjing, P. R. of China
Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers.

Angew. Chem. Int. Ed. 2017;
56: 637-640
CrossrefPubMedGoogle Scholar
Further Information

Publication History

Publication Date:
15 February 2017 (online)

 
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Key words

sarcandrolide J - shizukaol D - sesquiterpenoid [4+2] dimers - Diels–Alder reaction - Kornblum–DeLaMare rearrangement - singlet oxygen Diels–Alder reaction

Significance

Liu and co-workers report the first syntheses of members of the family of lindenane sesquiterpenoid [4+2] dimer family of natural products. Despite their structural similarity, sarcandrolide J and shizukaol D were isolated from different plant species. The bioinspired synthetic strategy relies on a key Diels–Alder cycloaddition.


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Comment

Diels–Alder reaction of dienophile C and the diene generated in situ from D yielded the desired diastereomer F in 83% yield. Intermediate G was subjected to singlet oxygen to afford H after Kornblum–DeLaMare rearrangement. Lactone methylation and acetylation completed the syntheses of sarcandrolide J and shizukaol D, respectively.


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