949892-17-5Relevant articles and documents
Combined directed metalation-cross coupling strategies. Total synthesis of the aglycones of gilvocarcin V, M and E
James, Clint A.,Snieckus, Victor
, p. 8149 - 8152 (1997)
Using the versatile Directed ortho and remote Metalation protocols linked with Suzuki-Miyaura cross coupling, efficient syntheses of defucogilvocarcin V, M, and E, 2-4 have been achieved.
A Novel Compound For Regulating Circadian Rhythm And A Use Thereof
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Paragraph 0033-0034; 0037-0038, (2017/10/20)
The present invention relates to a novel compound which shows activities dependent on a crucial gene Rev-erbandalpha; constituting biological clock, and enables the production of pharmaceutical compositions for regulating biorhythms containing the novel c
Combined directed remote metalation-transition metal catalyzed cross coupling strategies: The total synthesis of the aglycones of the gilvocarcins V, M, and E and arnottin I
James, Clint A.,Snieckus, Victor
experimental part, p. 4080 - 4093 (2009/09/30)
(Chemical Equation Presented) A key directed remote metalation (DreM)-carbamoyl migration strategy was applied in an efficient synthesis of the naturally occurring 6H-naphtho[1,2-b]benzopyran-6-one defucogilvocarcin V (1a, Scheme 11). The required biarylcarbamate 33d was best prepared by a high yielding Suzuki coupling reaction of 31a with the differentially protected trioxygenated naphthalene coupling partner 32d which was synthesized using a selective acylation of a juglone derivative. In the late stages of the synthesis, the triflate 39 served as the common intermediate to install the required C-8 vinyl group of 1a (Stille coupling) as well as the required substituents for the preparation of defucogilvocarcins M (1b) and E (1c). A variety of protecting group strategies were investigated and provided insight into which groups are preferred for the DreM-carbamoyl migration process. The strategic lessons learned from this total synthesis were applied in the successful total synthesis of the structurally similar natural product arnottin I (2).