US 11,866,398 B2
Total synthesis of prostaglandin J natural products by stereoretentive metathesis
Jiaming Li, Pasadena, CA (US); Xu Chen, Pasadena, CA (US); Tonia S. Ahmed, Pasadena, CA (US); Brian M. Stoltz, Pasadena, CA (US); and Robert H. Grubbs, Pasadena, CA (US)
Assigned to California Institute of Technology, Pasadena, CA (US)
Appl. No. 17/055,970
Filed by California Institute of Technology, Pasadena, CA (US)
PCT Filed May 14, 2019, PCT No. PCT/US2019/032259
§ 371(c)(1), (2) Date Nov. 16, 2020,
PCT Pub. No. WO2019/222244, PCT Pub. Date Nov. 21, 2019.
Claims priority of provisional application 62/803,603, filed on Feb. 11, 2019.
Claims priority of provisional application 62/671,891, filed on May 15, 2018.
Prior Publication US 2021/0332011 A1, Oct. 28, 2021
Int. Cl. C07C 405/00 (2006.01); B01J 23/46 (2006.01)
CPC C07C 405/0016 (2013.01) [B01J 23/462 (2013.01); C07C 2601/10 (2017.05)] 10 Claims
 
1. A method for producing at least one Δ12-Prostaglandin J product represented by Formula (IV),

OG Complex Work Unit Chemistry
wherein: Rz is selected from

OG Complex Work Unit Chemistry
 and wherein at least one carbon-carbon double bond has a Z/E-selectivity of 95/5, or 96/4, or 97/3, or 98/2, or 99/1, or >99/<1;
comprising, submitting an alcohol product of Formula (III)

OG Complex Work Unit Chemistry
to oxidation conditions; wherein the alcohol product of Formula (III) is formed during a cross-metathesis reaction between a substrate represented by Formula (II)

OG Complex Work Unit Chemistry
and cis-5-octen-1-ol in the presence of a ruthenium olefin metathesis catalyst; and wherein Rv is selected from

OG Complex Work Unit Chemistry