Synthesis of an isomer of the renieramycin skeleton from L‐tyrosine

A new approach that tried to obviate the use of bromine protection groups was studied to synthesize (−)-renieramycin G from L-tyrosine. It was found that the first intermolecular Pictet–Spengler reaction proceeded successfully to give the correct tetrahydroisoquinoline precursor 6. However, the second intramolecular Pictet–Spengler cyclization step failed to give the desired product, and an isomer of the skeleton of the renieramycins was obtained via 12 steps starting from L-tyrosine. J. Heterocyclic Chem., (2011).

[1]  W. Liu,et al.  Total synthesis of (–)‐MY 336a from L‐tyrosine , 2009 .

[2]  W. Liu,et al.  Total synthesis of (−)-renieramycin G from l-tyrosine , 2009 .

[3]  Robert M. Williams,et al.  Synthetic studies on Et-743. Assembly of the pentacyclic core and a formal total synthesis. , 2008, The Journal of organic chemistry.

[4]  G. Vincent,et al.  Regioselectivity of Pictet-Spengler Cyclization Reactions to Construct the Pentacyclic Frameworks of the Ecteinascidin-Saframycin Class of Tetrahydroisoquinoline Antitumor Antibiotics. , 2007, Tetrahedron letters.

[5]  Zhanzhu Liu,et al.  Synthesis and antitumor activity of simplified ecteinascidin-saframycin analogs. , 2006, Bioorganic & medicinal chemistry letters.

[6]  Zhanzhu Liu,et al.  A new efficient synthetic process for the construction of the pentacyclic core of marine alkaloid ecteinascidins , 2003 .

[7]  Robert M. Williams,et al.  Synthetic studies on ecteinascidin-743: constructing a versatile pentacyclic intermediate for the synthesis of ecteinascidins and saframycins. , 2003, Organic letters.

[8]  Robin M. Williams,et al.  Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. , 2002, Chemical reviews.

[9]  A. Kubo,et al.  A practical synthesis of the ABC ring model of ecteinascidins. , 2000, Chemical & pharmaceutical bulletin.

[10]  A. Myers,et al.  One-step construction of the pentacyclic skeleton of saframycin A from a "Trimer" of alpha-amino aldehydes. , 2000, Organic letters.

[11]  S. Danishefsky,et al.  Synthetic explorations in the saframycin-ecteinascidin series: construction of major chiral subunits through catalytic asymmetric induction , 2000 .

[12]  S. Danishefsky,et al.  A novel face specific Mannich closure providing access to the saframycin-ecteinascidin series of piperazine based alkaloids , 2000 .

[13]  E. Corey,et al.  A new, more efficient, and effective process for the synthesis of a key pentacyclic intermediate for production of ecteinascidin and phthalascidin antitumor agents. , 2000, Organic letters.

[14]  A. Myers,et al.  A Concise, Stereocontrolled Synthesis of (−)-Saframycin A by the Directed Condensation of α-Amino Aldehyde Precursors , 1999 .

[15]  B. Zhong,et al.  Preparation of Chiral, C-Protected α-Amino Aldehydes of High Optical Purity and Their Use as Condensation Components in a Linear Synthesis Strategy , 1999 .

[16]  T. Fukuyama,et al.  Synthetic Study on Ecteinascidin 743 Starting from d-Glucose , 1999 .

[17]  E. Corey,et al.  Enantioselective synthesis of saframycin A and evaluation of antitumor activity relative to ecteinascidin/saframycin hybrids. , 1999, Organic letters.

[18]  A. Myers,et al.  Greatly Simplified Procedures for the Synthesis of alpha-Amino Acids by the Direct Alkylation of Pseudoephedrine Glycinamide Hydrate. , 1999, The Journal of organic chemistry.

[19]  K. Yamaguchi,et al.  Synthesis of saframycins. XII. 1 total synthesis of (-)-N-acetylsaframycin Mx 2 and Its epi-(+)-enantiomer , 1995 .

[20]  N. Saito,et al.  Synthesis of saframycins. IX. , 1994 .

[21]  A. Kubo,et al.  Synthesis of saframycins. VIII: Synthesis of the ABC ring of safracins , 1992 .

[22]  B. Davidson,et al.  Renieramycin G, a new alkaloid from the sponge Xestospongia caycedoi , 1992 .

[23]  T. Shawe,et al.  Saframycin synthetic studies , 1991 .

[24]  R. Sachleben,et al.  Total synthesis of (.+-.)-saframycin A , 1990 .

[25]  A. Kubo,et al.  Synthesis of saframycins. 3. Preparation of a key tricyclic lactam intermediate to saframycin A , 1989 .

[26]  A. Kubo,et al.  Stereoselective total synthesis of (±)-saframycin B , 1988 .

[27]  A. Kubo,et al.  Synthesis of saframycins. II. Preparations and reactions of N-methyl-2,5-piperazinediones. , 1988, Chemical & pharmaceutical bulletin.

[28]  A. Kubo,et al.  Preparations and Reactions of (Z) -3-Arylidene-6-arylmethyl-2, 5-piperazinediones Having Highly Oxygenated Benzene Rings , 1987 .

[29]  A. Kubo,et al.  Synthesis of saframycins. I. Total synthesis (+/-)-saframycin B and its congeners. , 1987, Chemical & pharmaceutical bulletin.

[30]  H. Mishima,et al.  A synthesis of 4-cyano-hexahydro-1,5-imino-3-benzazocine-7,10-dione; a potential intermediate to saframycin synthesis , 1986 .

[31]  R. Sachleben,et al.  Stereocontrolled total synthesis of (.+-.)-saframycin B , 1982 .

[32]  A. Kubo,et al.  An Improved Synthesis of the ABC Ring Model of Ecteinascidins , 1999 .

[33]  K. Yamaguchi,et al.  SYNTHETIC APPROACHES TOWARD ECTEINASCIDINS. PART 1. PREPARATION OF AN (E)-2-ARYLIDENE-3-BENZYL-1,5-IMINO-3-BENZAZOCIN-4-ONE HAVING A PROTECTED PHENOL IN THE E-RING , 1997 .

[34]  T. Fukuyama,et al.  A stereocontrolled total synthesis of (±)-renieramycin A , 1990 .

[35]  A. Kubo,et al.  A promising cyclization of the 3-arylidene-6-arylmethyl-2,5-piperazinedione to construct tricyclic lactam as an intermediate to saframycin synthesis , 1987 .

[36]  H. Mishima,et al.  Studies directed towards total synthesis of saframycin: I. A synthesis of hexahydro-1,5-imino-3-benzazocin-7,10-dione. , 1982 .

[37]  P. G. Sammes,et al.  Some stereoselective and regioselective olefin additions: iodoacetoxylation and related electrophilic additions across the 22(23)-bond of 3 ,5 -cycloergosta-7,22-dien-6-one. , 1972, Journal of the Chemical Society. Perkin transactions 1.