96685-52-8Relevant academic research and scientific papers
Vitamin D3 synthetic studies. Intramolecular Diels-Alder approaches to the CD-ring fragment
Clasby, Martin C.,Craig, Donald,Jaxa-Chamiec, Albert A.,Lai, Justine Y. Q.,Marsh, Andrew,Slawin, Alexandra M. Z.,White, Andrew J. P.,Williams, David J.
, p. 4769 - 4802 (2007/10/03)
The enantiospecific synthesis of the vitamin D3 CD ring fragment 3 is reported. Key steps are the diastereoselective allylation of a norephedrine/dihydrocitronellic acid-derived oxazolidinone, and the intramolecular Diels-Alder reaction of a sulfonyl-substituted dienyne. The analogous cycloaddition reaction of a trienylsulfone substrate is shown to give products having the incorrect stereochemistry for vitamin D3 synthesis.
Vitamin D3 synthetic studies. A three-step procedure for the preparation of (+)-(1R,5R,6R,9R,2'R)-1-methyl-9-(6-methylhept-2-yl)-5- (phenylsulfonyl)bicyclo[4.3.0]nonane from Windaus-Grundmann ketone
Clasby,Craig
, p. 481 - 488 (2007/10/02)
A procedure is described for the preparation of vitamin D3 key fragment (+)-(1R,5R,6R,9R,2'R)-1-methyl-9-(6-methylhept-2-yl)-5- (phenylsulfonyl)bicyclo[4.3.0]nonane 3 in three steps and 55% overall yield from Windaus-Grundmann ketone 5.
A Novel Approach to the Stereocontrolled Synthesis of Steroid Side Chains Including the CD-Ring System: The First Total Synthesis of (+)-8α-(Phenylsulfonyl)des-AB-cholestane and Its Efficient Conversion into Grundmann's Ketone and Vitamin D3
Nemoto, Hideo,Kurobe, Hiroshi,Fukumoto, Keiichiro,Kametani, Tetsuji
, p. 5311 - 5320 (2007/10/02)
A new stereocontrolled approach to steroid CD-ring system including side chain starting from an optically active indenedione 6 is described.The application of this finding allows for the asymmetric synthesis of des-AB-cholestane 3 and 8α-(phenylsulfonyl)des-AB-cholestane 37; from the latter Grundmann's ketone 25 and vitamin D3 (27) were synthesized efficiently.
A GENERAL METHOD FOR THE STEREOSELECTIVE CONSTRUCTION OF DES-AB-CHOLESTANES. A FIRST TOTAL SYNTHESIS OF (+)-8α-PHENYLSULFONYL-DES-AB-CHOLESTANE
Nemoto, Hideo,Kurobe, Hiroshi,Fukomoto, Keiichiro,Kametani, Tetsuji
, p. 259 - 262 (2007/10/02)
(+)-8α-Phenylsulfonyl-des-AB-cholestane, a potential intermediate of vitamin D3, was stereoselectively synthesized from (-)-indanone derivative possessing the required chiralities, at the C13, C14, C17, and C20
A MODIFIED SYNTHESIS OF THE (+)-8α-PHENYLSULPHONYL-DES-AB-CHOLESTANE VIA AN INTRAMOLECULAR NUCLEOPHILIC ATTACK TO EPOXIDE - A TOTAL SYNTHESIS OF VITAMIN D3
Nemoto, Hideo,Kurobe, Hiroshi,Fukumoto, Keiichiro,Kametani, Tetsuji
, p. 567 - 569 (2007/10/02)
An intramolecular alkylation of the phenylsulphonyl epoxide (6), which was readily obtained from the alsehyde (5), gave a separable mixture of the alcohols (7a) and (8a).The alcohol (8a) was then dehydrated via the corresponding mesylate (8b) to afford th
