US 12,391,723 B2
Steroids and methods of manufacture
Glenn C. Micalizio, Hanover, NH (US)
Assigned to Trustees of Dartmouth College, Hanover, NH (US)
Filed by Trustees of Dartmouth College, Hanover, NH (US)
Filed on Aug. 10, 2022, as Appl. No. 17/818,873.
Application 17/818,873 is a division of application No. 16/637,675, granted, now 11,459,353, previously published as PCT/IB2018/056205, filed on Aug. 16, 2018.
Claims priority of provisional application 62/605,551, filed on Aug. 16, 2017.
Prior Publication US 2023/0018615 A1, Jan. 19, 2023
Int. Cl. C07J 11/00 (2006.01); A61P 35/00 (2006.01); C07J 15/00 (2006.01); C07J 75/00 (2006.01)
CPC C07J 11/00 (2013.01) [A61P 35/00 (2018.01); C07J 15/00 (2013.01); C07J 75/005 (2013.01)] 21 Claims
 
1. A method for making a compound of Formula (G):

OG Complex Work Unit Chemistry
the method comprising:
forming a B-ring by cyclopropanation and intramolecular Friedel-Crafts alkylation of an intermediate compound of Formula (E) using a compound of CH(X)3

OG Complex Work Unit Chemistry
wherein R1 is C1-C4 alkyl optionally substituted with a C6-C10 aryl; R3 is hydrogen, C1-C4 alkyl, halogen, or —O-(C1-C4-alkyl); R4 is trimethylsilyl; and X is halogen.