@article { ISI:000242873400039,
	title = {Stereoselective syntheses of unnatural steroidal C(20R) aldehydes by ionic hydrogenation of C-20 tertiary alcohols},
	journal = {Tetrahedron Letters},
	volume = {47},
	number = {52},
	year = {2006},
	month = {DEC},
	pages = {9343-9347},
	publisher = {PERGAMON-ELSEVIER SCIENCE LTD},
	type = {Article},
	address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND},
	abstract = {<p>Syntheses of three unnatural steroidal C(20R) aldehydes have been realised from 16-dehydropregnenol one acetate. The salient feature of the synthesis is the ionic hydrogenation of C-20 tertiary alcohols leading to the formation of the C(20R) unnatural isomer with complete stereoselectivity. Oxidative hydrolysis of the dithiane moiety furnished the C(20R) aldehydes. (c) 2006 Elsevier Ltd. All rights reserved.</p>},
	keywords = {1, 3-dithiane, ionic hydrogenation, oxidative hydrolysis, stereoselective synthesis, unnatural C-20 aldehydes},
	issn = {0040-4039},
	doi = {10.1016/j.tetlet.2006.10.116},
	author = {Shingate, Bapurao B. and Hazra, Braja G. and Pore, Vandana S. and Gonnade, Rajesh G. and Bhadbhade, Mohan M.}
}
@article {49507,
	title = {Studies on the stereoselective synthesis of sacubitril via a chiral amine transfer approach},
	journal = {Chemistry-An Asian Journal},
	volume = {20},
	year = {2025},
	month = {MAR },
	type = {Article},
	abstract = {<p>
	We present a comprehensive account of our efforts directed towards the synthesis of sacubitril, a neprilysin inhibitor used in combination with valsartan and marketed as Entresto (TM). Our initial approach to the formal synthesis of sacubitril employed a chiral pool strategy, utilizing (S)-pyroglutamic acid as a key building block and Cu(I)-mediated Csp2-Csp3 cross-coupling as a key transformation. Further investigations led to the development of chiral amine transfer (CAT) reagents-based stereoselective synthesis. This involved the E-selective construction of gamma-ylidene-butenolide from readily available biphenyl bromide and 4-pentynoic acid, the conversion of this butenolide to its ene-lactam using chiral amine, and substrate-controlled diastereoselective reduction of ene-lactam using Et3SiH or Pd/C, H2 (overall chiral amine transfer) as key transformations. Antipodal lactam intermediates were synthesized using corresponding chiral amines, and the stereochemical outcomes during the ene-lactam reduction with Et3SiH were rationalized by DFT studies.</p>
},
	keywords = {Chiral Amine Transfer (CAT) approach, Chiral pool approach, Sacubitril, stereoselective synthesis},
	issn = {1861-4728},
	doi = {10.1002/asia.202401223},
	author = {Sadanande, Megha V. and Thorat, Sagar S. and Sharma, Himanshu and Singh, Geetika and Vanka, Kumar and Gonnade, Rajesh G. and Kontham, Ravindar}
}
