929897-51-8Relevant articles and documents
Stereodivergent Hydroboration of Allenes
Nagashima, Yoshiyuki,Sasaki, Keiji,Suto, Takahiro,Sato, Takaaki,Chida, Noritaka
supporting information, p. 1024 - 1028 (2018/03/21)
Full details of a stereodivergent hydroboration of allenes are reported. While hydroboration of an allene with 9-BBN provided a thermodynamically stable (E)-allylic alcohol after oxidative work-up, the reaction of an identical allene with HB(Sia)2 (disiamylborane) formed a (Z)-allylic alcohol as the kinetic product. The developed conditions allowed for the synthesis of trisubstituted olefins in a highly stereoselective fashion, which is known to be challenging. The method was also applied to the stereodivergent synthesis of structural motifs such as skipped dienes and allylbenzenes, which are often embedded in biologically active natural products.
Concise Synthesis of the Tricyclic Core of Salimabromide
Schmalzbauer, Bj?rn,Menche, Dirk
, p. 2956 - 2959 (2015/06/30)
A concise synthesis of the tricyclic core 2 of the structurally unique marine myxobacterial natural product salimabromide has been developed. Compound 2 contains the tetraline subunit including the two quaternary centers and the eight-membered ring of sal
Synthesis of racemic Δ3-2-hydroxybakuchiol and its analogues
Shi, Lei,Lei, Xinsheng,Zhang, Jiange,Lin, Guoqiang
experimental part, p. 555 - 564 (2010/06/14)
The first synthetic approach to (±)-Δ3-2- hydroxybakuchiol (=4-[(1E,5E)-3-ethenyl-7-hydroxy-3,7-dimethylocta-1,5-dien-1- yl]phenol; 14) and its analogues 13a - 13f was developed by 12 steps (Schemes 2 and 3). The key features of the approach are the construction of the quaternary C-center bearing the ethenyl group by a Johnson - Claisen rearrangement (→6); and of an (E)-alkenyl iodide via a Takai - Utimoto reaction (→11); and an arylation via a Negishi cross-coupling reaction (→12e - 12f).