111865-84-0Relevant academic research and scientific papers
Stereochemical elucidation of the 1,4 polyketide amphidinoketide I.
Walsh, Louise M,Goodman, Jonathan M
, p. 2616 - 2617 (2003)
The relative and absolute stereochemistry of amphidinoketide I has been determined by the total synthesis of all the diastereoisomers. Molecular modelling suggests that the natural product is not the thermodynamically preferred diastereoisomer.
An Effective Bifunctional Aldehyde Linchpin for Type II Anion Relay Chemistry: Development and Application to the Synthesis of a C16-C29 Fragment of Rhizopodin
Melillo, Bruno,Chen, Ming Z.,Forestieri, Roberto,Smith, Amos B.
, p. 6242 - 6245 (2016/01/09)
The design, synthesis, and validation of a new bifunctional aldehyde linchpin for Type II anion relay chemistry have been achieved. For this linchpin, the initial nucleophilic addition proceeds under Felkin-Anh control to generate the syn-alkoxide, which
Synthesis of the macrocyclic core of (-)-pladienolide B
Skaanderup, Philip R.,Jensen, Thomas
supporting information; experimental part, p. 2821 - 2824 (2009/05/27)
(Chemical Equation Presented) An efficient synthesis of the macrocyclic core of (-)-pladienolide B is disclosed. The concise route relies on a chiral auxiliary-mediated asymmetric aldol addition and an osmium-catalyzed asymmetric dihydroxylation to install the three oxygenated stereocenters of the macrocycle. This purely reagent-controlled and flexible strategy sets the stage for future analogue syntheses and structure-activity relationship plotting of the appealing anticancer lead structure pladienolide B.
Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols
Zhang, Wei,Yamamoto, Hisashi
, p. 286 - 287 (2008/04/18)
New chiral bishydroxamic acids were synthesized and tested as chiral ligands in the vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols to provide good yields and high enantioselectivities. Copyright
Formal total synthesis of altohyrtin C (spongistatin 2). Part 1: Aldol approach to unite AB and CD spiroacetals
Terauchi, Takeshi,Terauchi, Taro,Sato, Ippei,Shoji, Wataru,Tsukada, Tomoharu,Tsunoda, Takashi,Kanoh, Naoki,Nakata, Masaya
, p. 7741 - 7745 (2007/10/03)
The Mukaiyama aldol coupling of the second-generation C1-C14 (AB) fragment of altohyrtins (spongistatins) with the model α-methyl-β -alkoxyaldehydes revealed that the stereochemistry at the newly formed carbon centers was controlled by the β-alkoxy chiral center of the model aldehydes. The union of the AB fragment with the C15-C28 (CD) fragment under the same conditions gave the fully elaborated C1-C28 (ABCD) subunit in good yield.
Synthesis of the C-1-C-28 ABCD Unit of Spongistatin 1
Gaunt, Matthew J.,Jessiman, Alan S.,Orsini, Paolo,Tanner, Huw R.,Hook, David F.,Ley, Steven V.
, p. 4819 - 4822 (2007/10/03)
(Equation Presented) The synthesis of the C-1-C-28 ABCD fragment of spongistatin is described. Anti-selective boron-mediated aldol coupling of a CD spiroketal ketone fragment to an AB spiroketal aldehyde unit forms the desired C1-C28 advanced intermediate
Room-temperature metallation of 2-substituted 1,3-dithiane derivatives and subsequent coupling with 2,3-disubstituted oxiranes
Ide, Mitsuaki,Nakata, Masaya
, p. 2491 - 2499 (2007/10/03)
2-Substituted 1,3-dithiane derivatives, (S)-1(t-butyldiphenylsiloxy)-2- (1,3-dithian-2-yl)propane (9), (S)-1-(t-butyldimethylsiloxy)-2-(1,3-dithian- 2-yl)propane, 1-(t-butyldiphenylsiloxy)-2-(1,3-dithian-2-yl)-2-methylpropane, and 1,2-bis-(t-butyldiphenylsiloxy)-3-(1,3-dithian-2-yl)propane, were subjected to lithiation in THF with n-BuLi at room temperature (r.t.); the resulting anions reacted with 2,3-disubstituted oxirane, trans-2-methyl-3- (triphenylmethoxymethyl)oxirane(22), at r.t., giving the coupling products in satisfactory yield. On the other hand, the lithium salt formed in ether from (S)2-(1,3-dithian-2-yl)-1-(4-methoxybenzyloxy)propane with n-BuLi at r.t. reacted with 22 at r.t. in the presence of hexamethylphosphoric triamide to afford the coupling product in moderate yield. In addition, a mixed organometallic reagent, n-BuLi/Bu2Mg, was found to be an effective metallation reagent for 9 and the resulting anion reacted with 22 to afford the coupling product in good yield.
Generation of 2-substituted-2-metallo-1,3-dithianes and their coupling with 1,2-disubstituted epoxides at room temperature
Ide, Mitsuaki,Yasuda, Minora,Nakata, Masaya
, p. 936 - 938 (2007/10/03)
2-Substituted-1,3-dithianes were subjected to lithiation by n-BuLi at room temperature and the resulting anions reacted with 1,2-disubstituted epoxides at room temperature, giving the coupling products in satisfactory yield. In addition, a mixed organomet
