Tags

Type your tag names separated by a space and hit enter

Total synthesis of (+)-crocacin D.
Org Lett. 2002 Feb 21; 4(4):525-7.OL

Abstract

[structure: see text] The first asymmetric synthesis of (+)-crocacin D (4) is described. The key steps in the sequence are the stereoselective assembly of the stereotetrad via a substrate-controlled aldol reaction and anti-selective reduction, formation of the (E,E)-diene by a Stille cross-coupling between the stannane 8 and vinyl iodide 9, and the acylation of (Z)-enecarbamate 6 with the acid chloride derived from polyketide fragment 16 which introduced the (Z)-enamide functionality.

Authors+Show Affiliations

Feutrill JT
School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
Lilly MJ
No affiliation info available
Rizzacasa MA
No affiliation info available

MeSH

AmidesAntifungal AgentsElectron TransportFungiIndicators and ReagentsMolecular Conformation

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

11843582

Citation

Feutrill, John T., et al. "Total Synthesis of (+)-crocacin D." Organic Letters, vol. 4, no. 4, 2002, pp. 525-7.
Feutrill JT, Lilly MJ, Rizzacasa MA. Total synthesis of (+)-crocacin D. Org Lett. 2002;4(4):525-7.
Feutrill, J. T., Lilly, M. J., & Rizzacasa, M. A. (2002). Total synthesis of (+)-crocacin D. Organic Letters, 4(4), 525-7.
Feutrill JT, Lilly MJ, Rizzacasa MA. Total Synthesis of (+)-crocacin D. Org Lett. 2002 Feb 21;4(4):525-7. PubMed PMID: 11843582.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Total synthesis of (+)-crocacin D. AU - Feutrill,John T, AU - Lilly,Michael J, AU - Rizzacasa,Mark A, PY - 2002/2/15/pubmed PY - 2002/4/16/medline PY - 2002/2/15/entrez SP - 525 EP - 7 JF - Organic letters JO - Org Lett VL - 4 IS - 4 N2 - [structure: see text] The first asymmetric synthesis of (+)-crocacin D (4) is described. The key steps in the sequence are the stereoselective assembly of the stereotetrad via a substrate-controlled aldol reaction and anti-selective reduction, formation of the (E,E)-diene by a Stille cross-coupling between the stannane 8 and vinyl iodide 9, and the acylation of (Z)-enecarbamate 6 with the acid chloride derived from polyketide fragment 16 which introduced the (Z)-enamide functionality. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/11843582/Total_synthesis_of__+__crocacin_D_ L2 - https://doi.org/10.1021/ol017092x DB - PRIME DP - Unbound Medicine ER -