154674-77-8Relevant academic research and scientific papers
BRYOSTATIN ANALOGS AND USE THEREOF AS ANTIVIRAL AGENTS
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Paragraph 0232; 0233, (2016/02/29)
Described herein are tricyclic macrolactones. The macrolactones have a high binding affinity for PKC. The compounds described herein can be used in a number of therapeutic applications including the treatment or prevention of viral infection. Also described herein are methods for producing macrolactones. The methods permit the high-yield synthesis of macrolactones in a low number of steps and with a high degree of substitution and specificity.
Total synthesis of GEX1A
Murray, Timothy J.,Forsyth, Craig J.
supporting information; experimental part, p. 3429 - 3431 (2009/05/11)
(Chemical Equation Presented) An efficient and readily modifiable synthesis of GEX1A/herboxidiene/TAN-1609 (1) was developed. This modular synthesis featured a Suzuki coupling to install the conjugated diene and a Ru-catalyzed lactonization and Roush crotylation to construct the functionalized tetrahydropyran moiety. Myers' alkylation, cross-metathesis, and Keck crotylation were employed for assembly of the biologically essential side-chain domain.
Synthetic studies on the bryostatins: Preparation of a truncated BC-ring intermediate by pyran annulation
Keck, Gary E.,Truong, Anh P.
, p. 2149 - 2152 (2007/10/03)
(Chemical Equation Presented) A synthesis of a potential BC-ring subunit (C9-C27) for bryostatin 1, a remarkably potent anticancer agent, has been developed in 16 steps and 18% overall yield. The key features of this route include a BITIP-catalyzed asymmetric allylation reaction, chelation-controlled allylations, a hydroformylation reaction, and a pyran annulation reaction.
Stereoselective synthesis of allylic amines by rearrangement of allylic trifluoroacetimidates: Stereoselective synthesis of polyoxamic acid and derivatives of other α-amino acids
Savage, Ian,Thomas, Eric J.,Wilson, Peter D.
, p. 3291 - 3303 (2007/10/03)
On heating in xylene under reflux, allylic trifluoroacetimidates undergo [3,3] sigmatropic rearrangement to regioisomeric allylic trifluoroacetamides. Examples include the rearrangements of the trifluoroacetimidates 16 and 73 to the trifluoroacetamides 17 and 74, which were incorporated into stereoselective syntheses of polyoxamic acid 1, and the rearrangement of the trifluoroacetimidate 26. The rearrangement was the key step in asymmetric syntheses of the (S)- and (R)-valine derivatives 37 and 48. Other examples include rearrangements of the trifluoroacetimidates 52, 54 and 56 prepared from geraniol, cinnamyl alcohol and sorbyl alcohol, respectively, and the more complex trifluoroacetimidates 62 and 69. The stereoselectivity of these rearrangements, which are somewhat faster than rearrangements of analogous allylic trichloroacetimidates, is consistent with the participation of chair-like, six-membered, transition structures. The Royal Society of Chemistry 1999.
Approaches to a synthesis of galbonolide B
Smith, Peter M.,Thomas, Eric J.
, p. 3541 - 3556 (2007/10/03)
An approach to the C(7)-C(15) fragment of galbonolide B 2 has been completed in which the diene fragment 51 was assembled from (R)-3-tert-butyldimethylsilyloxypentan-2-one 29 by conversion into the unsaturated ester 30, acylation of the sulfone 47 using this ester, reductive desulfurisation, methylenation using a Wittig reaction and deprotection. Following model studies, the aldehyde 62, prepared by oxidation of the alcohol 51, was converted into a mixture of the epimeric alcohols 63 and these were converted into the di(methylene)tridecadienoic acid 65 using a phosphine catalysed Ireland-Claisen rearrangement. Sharpless epoxidations of the alcohol 67 using either L-(+)- or D-(-)-diethyl tartrate were highly stereoselective and gave the epoxides 68 and 69 which were clearly distinguishable. Model studies using the heptadiene monoepoxide 70 led to a synthesis of the monoprotected dihydroxy aldehyde 76 so establishing a protocol for the introduction into the vicinal diol of the galbonolides. Finally, aldol addition of tert-butyl acetate to the aldehyde 78 followed by selective protection, deprotection and cyclisation completed a synthesis of the macrolide 85.
Asymmetric α-Aminoacid Synthesis using Rearrangement of Allylic Trifluoroacetimidates: Synthesis of Thymine Polyoxin C
Chen, Anqi,,Savage, Ian,Thomas, Eric J.,Wilson, Peter D.
, p. 6769 - 6772 (2007/10/02)
Improved procedures are reported for the synthesis of chiral trifluoroacetimidates and are applied to complete a total synthesis of thymine polyoxin C.
