97143-16-3Relevant academic research and scientific papers
Ring expansions of β-keto lactones with zinc carbenoids: Syntheses of (+)-patulolide A and (±)-patulolide B
Ronsheim, Matthew D.,Zercher, Charles K.
, p. 1878 - 1885 (2003)
A one-pot ring expansion/oxidation/elimination method has been developed in which β-keto lactones are converted efficiently to α,β-unsaturated-γ-keto lactones. The reaction can be successfully applied to a variety of ring sizes. Alkene stereochemistry is dependent upon ring size and reaction conditions. The method was applied to the synthesis of (+)-patulolide A.
An alternative total synthesis of Patulolide A
Konidena, Lakshmi Narayana Sharma,Chettu, Suresh Kumar,Mukkavilli, Praveena,Valluru, Krishna Reddy,Kameswara Rao,Nowduri, Annapurna,Korupolu, Raghu Babu
, p. 226 - 230 (2019)
A new total synthesis of [R]-Patulolide A from readily available (R)-propylene epoxide obtained using the asymmetric synthetic approach is reported. The key reactions involved are ozonolysis and Yamaguchi macrolactonization, resulting in the ring system.
Total synthesis of patulolide A through ring closing metathesis
Subhashini,Bhadraiah,Janaki,Sridhar, Gattu
, p. 496 - 499 (2018/02/14)
A simple and efficient total synthesis of patulolide A from readily available 7-octen-1-ol is reported by asymmetric synthetic approach. The key reactions involved are asymmetric dihydroxylation using AD-mix-β and Grubbs’ ring-closing metathesis reaction
Total synthesis of R-(+)-patulolide A and R-(-)-patulolide B: The macrolides isolated from Penicillium urticae mutant
Kalita, Dipak,Khan, Abu Taleb,Barua, Nabin C.,Bez, Ghanashyam
, p. 5177 - 5184 (2007/10/03)
The title compounds (2E,11R)-4-oxo-2-dodecen-11-olide, 1 and (2Z,11R)- 4-oxo-2-dodecen-11-olide, 2 were synthesised in optically pure forms from a nitroalkane synthon involving a chiral resolution step using goat liver lipase.
Chemoenzymatic synthesis of (R)-(+)-Patulolide A, a macrolide antibiotic isolated from Penicillium urticae
Kamezawa, Makoto,Kitamura, Masaya,Nagaoka, Hiroyuki,Tachibana, Hojun,Ohtani, Takehiko,Naoshima, Yoshinobu
, p. 167 - 170 (2007/10/03)
(R)-(+)-Patulolide A [(R)-1] was synthesized with an enantiomeric purity of almost 100% e.e. by a two-step lipase-catalyzed enantioselective hydrolysis of racemic thioketal acetate (±)-11. VCH Verlagsgesellschaft mbH, 1996.
Expedient synthesis of (R)-patulolide A
Sharma,Sankaranarayanan,Chattopadhyay
, p. 1814 - 1816 (2007/10/03)
An efficient derivation of the title compound has been formulated from easily accessible 10-undecenoic acid (1). Thus, dodec-11-en-2-ol (3), prepared from 1, was pyranylated and subjected to bromination with NBS followed by acetolysis to furnish (2E)-1-acetoxy-11-(tetrahydropyranyloxy)dodec-2-ene (5). Its hydrolysis, oxidation, and depyranylation afforded the (2E)-hydroxy ester (9). This, on Candida rugosa lipase-catalyzed acetylation, SeO2 oxidation, hydrolysis, and Yamaguchi macrolactonization, led to (R)-patulolide A (l) with 67.1% ee. The enantiomeric excess was improved to 97% by first resolving the alcohol 3 via porcine pancreatic lipase catalyzed acetylation and converting the corresponding (R)-acetate (13) to I as done above.
Synthesis of (R)-(+)-patulolide A
Bestmann,Kellermann,Pecher
, p. 149 - 152 (2007/10/02)
A new total synthesis of (R)-(+)-patulolide A [(11R,2E)-4-oxo-2-dodecen-11-olide] using the cyclization of hydroxy aldehydes with ketenylidenetriphenylphosphorane is described.
Synthetic Microbial Chemistry, XVI. - Synthesis of Patulolides A, B, and C, New Macrolides Isolated from Penicillium urticae
Mori, Kenji,Sakai, Teruyuki
, p. 13 - 18 (2007/10/02)
An enantioselective synthesis of patulolide A (1), patulolide B (2), and patulolide C (3) from ethyl (R)-3-hydroxybutanoate is described.
