General Synthetic Entry to Dihydrooxepine-spiroisoxazoline Natural Products: Total Synthesis of Psammaplysin A

Autor:	Thomas Magauer, Jan Paciorek, Kevin Sokol, Denis Hoefler, Klaus Wurst
Rok vydání:	2022
DOI:	10.26434/chemrxiv-2022-px26h-v2
Popis:	Here, we report a general synthetic entry to dihydrooxepine-spiroisoxazoline (DOSI) natural products that culminated in the first total synthesis of psammaplysin A. For the synthesis of the unique spirocyclic fragment we employed a strategy that features two key transformations: (1) The use of a diastereoselective Henry reaction/cyclization sequence granted access to the C7 hydroxylated isoxazoline scaffold in one step. (2) A regioselective Baeyer–Villiger ring expansion enabled selective installation of the fully substituted dihydrooxepine and avoided the risk of a previously observed oxepine-arene oxide rearrangement. The overall synthesis proceeds in 13 steps from inexpensive starting material.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::687c74e67c3a51aff1ca5756757423b4 https://doi.org/10.26434/chemrxiv-2022-px26h-v2 Zobrazit plný text záznamu