Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products | Zendy

Ivica Zamarija | Zendy; Benjamin J. Marsh | Zendy; Thomas Magauer | Zendy

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Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products

Author(s) -

Ivica Zamarija,

Benjamin J. Marsh,

Thomas Magauer

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.1c03530

Subject(s) - chemistry , regioselectivity , ring (chemistry) , combinatorial chemistry , reaction conditions , functional group , protocol (science) , organic chemistry , catalysis , medicine , alternative medicine , pathology , polymer

Herein, we describe a two-step ring expansion of 1-indanones to afford 2-chloro/bromo-1-naphthols (32 examples). The developed method shows broad functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natural products. The orthogonally functionalized products allow for selective postmodifications as exemplified in the total synthesis of defucogilvocarcin M. For the selective oxidation of the chromene, a mild and regioselective oxidation protocol (DDQ and TBHP) was developed.

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