119650-51-0Relevant articles and documents
Boron-selective biaryl coupling approach to versatile dibenzoxaborins and application to concise synthesis of defucogilvocarcin M
Sumida, Yuto,Harada, Ryu,Kato-Sumida, Tomoe,Johmoto, Kohei,Uekusa, Hidehiro,Hosoya, Takamitsu
, p. 6240 - 6243 (2014)
An efficient synthetic method for versatile dibenzoxaborins based on boron-selective Suzuki-Miyaura cross-coupling between o-borylphenols and aryl halides or triflates bearing a 1,8-diaminonaphthalene-protected o-boryl group is reported. A short synthesis
Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
Zamarija, Ivica,Marsh, Benjamin J.,Magauer, Thomas
, p. 9221 - 9226 (2021/11/30)
Herein, we describe a two-step ring expansion of 1-indanones to afford 2-chloro/bromo-1-naphthols (32 examples). The developed method shows broad functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natural products. The orthogonally functionalized products allow for selective postmodifications as exemplified in the total synthesis of defucogilvocarcin M. For the selective oxidation of the chromene, a mild and regioselective oxidation protocol (DDQ and TBHP) was developed.
A xanthate-based free radical approach to defucogilvocarcin M
Cortezano-Arellano, Omar,Cordero-Vargas, Alejandro
supporting information; experimental part, p. 602 - 604 (2010/04/05)
A formal total synthesis of the aglycon of gilvocarcin M is described. The synthesis is based on the construction of the key naphthalene 7 via a free radical addition-cyclization protocol followed by aromatization of the resulting α-tetralone. This highly
Concise three-component synthesis of defucogilvocarcin M
Takemura, Isao,Imura, Koreaki,Matsumoto, Takashi,Suzuki, Keisuke
, p. 2503 - 2505 (2007/10/03)
(Matrix Presented) Concise synthesis of defucogilvocarcin M was achieved via the [2 + 2 + 2] approach to β-phenylnaphthalene structure.
A concise total synthesis of the aglycone of the gilvocarcins
Deshpande, Prashant P.,Martin, Olivier R.
, p. 6313 - 6316 (2007/10/02)
A brief and convergent synthesis of the aglycone of the gilvocarcins M and E (and formally V) involving, in the key step, a Pd-mediated intramolecular biaryl coupling, is reported.
A New Synthesis of Defucogilvocarcin M
Hart, David J.,Merriman, Gregory H.
, p. 5093 - 5096 (2007/10/02)
A convergent synthesis of the title compound is described.The synthesis revolves around a MAD-mediated coupling of oxazoline 11 and naphthoquinone ketal 16 and requires eight steps via the longest linear sequence.