185197-80-2Relevant articles and documents
Stereoselective Palladium-Catalyzed Approach to Vitamin D3 Derivatives in Protic Medium
Carballa, Diego,Sigüeiro, Rita,Rodríguez-Docampo, Zaida,Zacconi, Flavia,Maestro, Miguel A.,Mouri?o, Antonio
, p. 3314 - 3320 (2018/02/12)
We describe an efficient convergent synthesis of vitamin D3 metabolites and analogues. The synthetic strategy relies on a tandem Pd-catalyzed A-ring closure and Suzuki–Miyaura coupling to the CD-side chain component to set directly the vitamin D triene system under protic conditions. This strategy enables rapid access to vitamin D3 and 3-epi-vitamin D3 metabolites and analogues modified at the side chain for biological evaluation and structural and metabolic studies.
An expedient procedure for the oxidative cleavage of olefinic bonds with PhI(OAc)2, NMO, and Catalytic OsO4
Nicolaou,Adsool, Vikrant A.,Hale, Christopher R. H.
supporting information; experimental part, p. 1552 - 1555 (2010/06/16)
(Figure Presented) PhI(OAc)2 In the presence of OsO4 (cat.) and 2,6-lutidine cleaves oleflnlc bonds to yield the corresponding carbonyl compounds, albeit, In some cases, with a-hydroxy ketones as byproduct. A more practical and clean protocol to effect oxidative cleavage of olefinic bonds involves NMO, OsO4 (cat.), 2,6-lutidine, and PhI(OAc) 2.
Synthesis and absolute configuration of rotundial, a mosquito repellent from the leaves of vitex rotundiforia
Takikawa, Hirosato,Yamazaki, Yuichiro,Mori, Kenji
, p. 229 - 232 (2007/10/03)
The enantiomers of rotundial (1), a mosquito repellent from the leaves of Vitex rotundiforia, were synthesized from the enantiomers of limonene oxide (2). The absolute configuration of natural rotundial was determined to be R.
Ozonides of mono-, bi- and tricyclic terpenes
Griesbaum, Karl,Hilss, Michael,Bosch, Joachim
, p. 14813 - 14826 (2007/10/03)
Ozonolysis of (+)-limonene (1) afforded a monoozonide 2 by attack of ozone at the internal double bond and two diastereomeric diozonides (3). Ozonolysis of 1 on polyethylene gave diozonides 3, and ozonolysis on silica gel gave an epoxy ozonide 5. Ozonolyses of (-)-β-pinene (15), (+)-sabinene (20) and (+)-aromadendrene (23) gave two diastereomers, each, of the corresponding ozonides 16, 21 and 24, respectively. Ozonolysis of camphene (26) gave a very labile ozonide 27, while ozonolysis of (-)-α-pinene (12) gave no ozonide. Ozonolysis of (+)-limonene (1) in the presence of formaldehyde gave a cross-ozonide (4), derived from ozone cleavage of the internal double bond, and ozonolysis of (-)-β-pinene in the presence of acetaldehyde also gave a cross-ozonide (17).
