124010-06-6Relevant academic research and scientific papers
Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis
Ochiai, Koji,Kuppusamy, Sankar,Yasui, Yusuke,Harada, Kenji,Gupta, Nishant R.,Takahashi, Yohei,Kubota, Takaaki,Kobayashi, Jun'ichi,Hayashi, Yujiro
supporting information, p. 3287 - 3291 (2016/03/05)
The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.
An efficient strategy for the synthesis of syn 1,3-diols via iterative acetate aldol reactions and synthesis of atorvastatin lactone
Goyal, Sandeep,Patel, Bhautikkumar,Sharma, Ratnesh,Chouhan, Mangilal,Kumar, Kapil,Gangar, Mukesh,Nair, Vipin A.
, p. 5409 - 5412 (2015/09/15)
An efficient strategy for the synthesis of syn 1,3-diol has been developed, employing an imidazolidinone based chiral auxiliary via stereoselective and sequential double acetate aldol reactions. The syn 1,3-diol subunit was modified to obtain the C-7 carboxylic acid side chain and further subjected to reaction with a suitable 1,4-diketone under Paal-Knorr conditions to obtain atorvastatin lactone.
Synthesis of the griseusin B framework via a one-pot annulation- methylation-double deprotection-spirocyclization sequence
Naysmith, Briar J.,Brimble, Margaret A.
supporting information, p. 2006 - 2009 (2013/06/04)
A highly convergent synthesis of the griseusin B scaffold is described. The key step involves an efficient one-pot Hauser-Kraus annulation-methylation- double deprotection-spirocyclization sequence that directly affords the target parent tetracyclic ring system.
Tetrahydropyran synthesis by intramolecular conjugate addition to enones: Synthesis of the clavosolide tetrahydropyran ring
Bates, Roderick W.,Song, Ping
experimental part, p. 2935 - 2942 (2010/10/21)
The synthesis of a tetrahydropyran intermediate for clavosolide A is reported, employing a combination of cross-metathesis and intramolecular oxa-Michael addition. The intramolecular oxa-Michael addition to ,-unsaturated esters requires the use of strong bases and can result in either modest yields or stereoisomeric mixtures, and can be highly variable according to the substrate structure. In contrast, the corresponding ketones cyclise under very mild conditions to give the 2,6-cis-isomers directly. The use of appropriately substituted ketones allows efficient conversion into esters.
Synthetic studies of complex immunostimulants from Quillaja saponaria: Synthesis of the potent clinical immunoadjuvant QS-21Aapi
Kim, Yong-Jae,Wang, Pengfei,Navarro-Villalobos, Mauricio,Ronde, Bridget D.,Derryberry, JohnMark,Gin, David Y.
, p. 11906 - 11915 (2007/10/03)
QS-21 is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing vaccine therapy clinical trials involving QS-21 as a critical adjuvant component for immune response augmentation. QS-21 is a natural product immunostimulatory adjuvant, eliciting both T-cell- and antibody-mediated immune responses with microgram doses. Herein is reported the synthesis of QS-21 Aapi in a highly modular strategy, applying novel glycosylation methodologies to a convergent construction of the potent saponin immunostimulant. The chemical synthesis of QS-21 offers unique opportunities to probe its mode of biological action through the preparation of otherwise unattainable nonnatural saponin analogues.
Stereoselective total synthesis of (+)-cryptocarya diacetate by an iterative Jacobsen's hydrolytic kinetic resolution protocol
Krishna, Palakodety Radha,Reddy, V. V. Ramana
, p. 3905 - 3907 (2007/10/03)
A combination of iterative Jacobsen's hydrolytic kinetic resolution and reduction of a ketone for the construction of a 1,3-polyol moiety are key steps en route to a total synthesis of (+)-cryptocarya diacetate.
