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Total Synthesis of Hybridaphniphylline B

Total Synthesis of Hybridaphniphylline B

Wenhao Zhang, Ming Ding, Jian Li, Zhicong Guo, Ming Lu, Yu Chen, Lianchao Liu, Yun-Heng Shen, Ang Li

J Am Chem Soc. 2018 Mar 28;140(12):4227-4231.

PMID: 29494142

Abstract:

Hybridaphniphylline B (1) is a Daphniphyllum alkaloid possessing 11 rings and 19 stereocenters. Here we report the first total synthesis of 1 featuring a late-stage intermolecular Diels-Alder reaction of a fully elaborated cyclopentadiene and asperuloside tetraacetate. The diene was prepared on the basis of a scalable route to daphnilongeranin B (4). Claisen rearrangement of an allyl dienol ether was exploited as a key step; the subtle variation of the substrate and use of protic solvents suppressed the undesired Cope rearrangement. Daphniyunnine E (6) and dehydrodaphnilongeranin B (7), two congeners of 4, were also synthesized. The dienophile arose from (+)-genipin through glycosylation and lactonization. A one-pot protocol was developed for the diene formation and Diels-Alder reaction; one of the cycloadducts was converted into 1 through reductive desulfurization and global deacetylation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP14259451	Asperuloside		14259-45-1	Price

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