Synthesis, Inhaltsverzeichnis Synthesis 2017; 49(23): 5231-5237DOI: 10.1055/s-0036-1588557 paper © Georg Thieme Verlag Stuttgart · New York An Enantioselective Synthesis of (5S,6R,11S,14R)-Acremodiol Papiya Dey Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India eMail: anubhas@barc.gov.in , Sucheta Chatterjee Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India eMail: anubhas@barc.gov.in , Sunita S. Gamre Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India eMail: anubhas@barc.gov.in , Subrata Chattopadhyay Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India eMail: anubhas@barc.gov.in , Anubha Sharma* Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India eMail: anubhas@barc.gov.in › Institutsangaben Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik § Equal contributions. Abstract An expeditious synthesis of the (5S,6R,11S,14R)-isomer of acremodiol was developed via a convergent route. One of the required building blocks was synthesized earlier via two sequential lipase-catalyzed secondary carbinol acetylations. The other unit was derived from (R)-2,3-cyclohexylideneglyceraldehyde as a chiral template. The bismacrolide skeleton was constructed by an intermolecular esterification reaction under Mitsunobu conditions followed by a ring-closing metathesis of the resultant α,ω-dialkenoic ester. Keywords Keywordsasymmetric synthesis - (R)-2,3-cyclohexylideneglyceraldehyde - macrodiolide - ring-closing metathesis - lipase-catalyzed transesterification Volltext Referenzen References 1 Blunt JW. Copp BR. Munro MH. G. Northcote PT. Prinsep MR. Nat. Prod. Rep. 2005; 22: 15 2a Õmura S. In Macrolide Antibiotics. Chemistry, Biology and Practice . Õmura S. Academic Press; Orlando: 1984: 509 2b Paterson I. Mansuri MM. Tetrahedron 1985; 41: 3569 2c Tadashi N. In Macrolide Antibiotics: Chemistry, Biology and Practice . 2nd ed.; Õmura S. Academic Press; San Diego: 2002: 181 3a Berg A. Notni J. Dorfelt H. Grafe U. J. Antibiot. 2002; 55: 660 ; and references cited therein 3b Grove JF. Speake RN. Ward G. J. Chem. Soc. 1966; 230 3c Sharma GV. M. Mallesham S. Chandra Mouli C. Tetrahedron: Asymmetry 2009; 20: 2513 4a Kumara Swamy KC. Bhuvan Kumar NN. Balaraman E. Pavan Kumar KV. P. Chem. Rev. 2009; 109: 2551 4b Dembinski R. Eur. J. Org. Chem. 2004; 2763 5 Chatterjee S. Ghadigaonkar S. Sur P. Sharma A. Chattopadhyay S. J. Org. Chem. 2014; 79: 8067 6a Salaskar A. Sharma A. Chattopadhyay S. Tetrahedron: Asymmetry 2005; 17: 325 6b Sharma A. Gamre S. Chattopadhyay S. Tetrahedron Lett. 2007; 48: 633 6c Sharma A. Gamre S. Chattopadhyay S. Tetrahedron Lett. 2007; 48: 3705 6d Roy S. Sharma A. Mula S. Chattopadhyay S. Chem. Eur. J. 2009; 15: 1713 6e Goswami D. Chattopadhyay A. Chattopadhyay S. Tetrahedron: Asymmetry 2009; 20: 1957 6f Biswas S. Chattopadhyay S. Sharma A. Tetrahedron: Asymmetry 2010; 21: 27 6g Goswami D. Sur P. Chattopadhyay A. Sharma A. Chattopadhyay S. Synthesis 2011; 1626 6h Reddy VV. Reddy BV. S. Helv. Chim. Acta 2016; 99: 636 6i Chattopadhyay A. J. Org. Chem. 1996; 61: 6104 6j Chatterjee S. Kanojia SV. Chattopadhyay S. Sharma A. Tetrahedron: Asymmetry 2011; 22: 367 6k Chattopadhyay A. Mamdapur VR. J. Org. Chem. 1995; 60: 585 7 Benaglia M. Caporale M. Puglisi A. Enantiomer 2002; 7: 383 8a Mohapatra DK. Reddy DS. Mallampudi NA. Gaddam J. Polepalli S. Jain N. Yadav JS. Org. Biomol. Chem. 2014; 12: 9683 8b Evans DA. Burch JD. Org. Lett. 2001; 3: 503 9a Srilatha M. Das B. Helv. Chim. Acta 2015; 98: 267 9b Bujaranipalli S. Eppa GC. Das S. Synlett 2013; 24: 1117 9c Martinelli MJ. Nayyar NK. Moher ED. Dhokte UP. Pawlak JM. Vaidyanathan R. Org. Lett. 1999; 1: 447 10a Crouch RD. Tetrahedron 2013; 69: 2383 10b Bhatt U. Christmann M. Quitschalle M. Claus E. Kalesse M. J. Org. Chem. 2001; 66: 1885 11a Gradillas A. Perez-Castells J. Angew. Chem. Int. Ed. 2006; 45: 6086 11b Chatterjee AK. Choi T.-L. Sanders DP. Grubbs RH. J. Am. Chem. Soc. 2003; 125: 11360 12 Zhu B. Panek JS. Org. Lett. 2000; 2: 2575 13a Hori H. Nishida Y. Ohrui H. Meguro H. J. Org. Chem. 1989; 54: 1346 13b Radha Krishna P. Reddy PV. N. Tetrahedron Lett. 2006; 47: 7473 13c Gurjar MK. Nagaprasad R. Ramana CV. Tetrahedron Lett. 2003; 44: 2873 Zusatzmaterial Zusatzmaterial Supporting Information
