Synthetic Studies of the Daphniphyllum Alkaloids: A Cooperative Reaction of Proximal Functional Groups Forming a Tetracyclic System

Ryosuke Yamada, Tohru Fukuyama, Satoshi Yokoshima

Organic Letters · 2018 · 10.1021/acs.orglett.8b01800

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★ 2.0 1 rating
5 : Major extension (new functional group) –
4 : Minor extension (no new functional group) –
3 : Reproduced as published –
2 : Reproduced with deviation ×1
1 : Did not work –
– : Extension failed / Inconclusive –

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PhD student
13 Jul 2026
★ 2 : Reproduced with deviation

We have attempted the resynthesis of S3, however, for us it was not possible to isolate the iodide given the low boiling point of the product. Thus it was used as crude in the next step without purification.
The iodide in the crude was estimated to be ~50%, which is in accordance with the reported yield.