72164-71-7Relevant academic research and scientific papers
Total Synthesis of Pulvomycin D
Fritz, Lukas,Wienhold, Sebastian,Hackl, Sabrina,Bach, Thorsten
supporting information, (2021/12/10)
A synthetic route to the pulvomycin class of natural products is presented, which culminated in the first synthesis of a pulvomycin, pulvomycin D. Key elements of the strategy include a pivotal aldol reaction which led to bond formation between the C24-C40 and the C8-C23 fragment. The remaining C1-C7 fragment was attached by a Yamaguchi esterification completing the assembly of the 40 carbon atoms within the main skeleton. Ring closure to the 22-membered lactone ring was achieved in the final stages of the synthesis by a Heck reaction. The completion of the synthesis required the removal of six silyl protecting groups in combination with olefin formation at C26-C27 by a Peterson elimination.
A new route for the synthesis of (R)-glyceraldehyde acetonide: A key chiral building block
Babu, K. Chandra,Ramadasu,Gangaiah,Madhusudhan,Mukkanti
experimental part, p. 260 - 263 (2010/10/20)
A new route for the synthesis of (R)-glyceraldehyde acetonide via asymmetric dihydroxylation of allyl 4-methoxybenzoate using the (DHQ) 2PHAL, K2OsO4·2H2O catalyst system is described. This route involves the asymmetric dihydroxylation of allyl-methoxybenzoate, acetonide protection of vicinyl dihydroxyl groups followed by cleavage of p-methoxybenzoate ester and subsequent oxidation to give the (R)-glyceraldehyde acetonide.
Stereoselective synthesis of anti-N-protected 3-amino-1,2-epoxides by nucleophilic addition to N-tert-butanesulfinyl imine of a glyceraldehyde synthon
Harried, Scott S.,Croghan, Michael D.,Kaller, Matthew R.,Lopez, Patricia,Zhong, Wenge,Hungate, Randall,Reider, Paul J.
experimental part, p. 5975 - 5982 (2009/12/24)
(Chemical Equation Presented) A di-O-TBS protected glyceraldehyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction of various R groups. The Ellman adducts were converted to useful multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2- epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.
