Correction to: Total synthesis of (-)-Sarain A (Journal of the American Chemical Society (2007) 129 (11987-12002) DOI: 10.1021/ja074300t);Total synthesis of (-)-sarain A

Journal of the American Chemical Society

Volumn 129, Issue 39, 2007, Pages 11987-12002

  Becker, Michael H ^a,b   Chua, Peter ^a,c   Downham, Robert ^a,d   Douglas, Christopher J ^a,e   Garg, Neil K ^a,f   Hiebert, Sheldon ^a,g   Jaroch, Stefan ^a,h   Matsuoka, Richard T ^a,i   Middleton, Joy A ^a,j   Ng, Fay W ^a,k   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BASF SE   (Germany)

^c Cylene Pharmaceuticals   (United States)

^d F2G LTD   (United Kingdom)

^e UNIVERSITY OF MINNESOTA   (United States)

^f UNIVERSITY OF CALIFORNIA   (United States)

^g BRISTOL MYERS SQUIBB   (United States)

^h BAYER PHARMA AG   (Germany)

ⁱ GLAXOSMITHKLINE   (United States)

^j GENENTECH INC   (United States)

^k Och Spine at New York Presbyterian Hospitals   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARBON; COMPLEXATION; SYNTHESIS (CHEMICAL);

PROXIMITY INTERACTION; QUATERNARY CARBON;

STEREOCHEMISTRY;

ALDEHYDE; ALKALOID; AMINE; DIAZATRICYCLOUNDECANE; ENOXYSILANE N SULFONYLIMINIUM; MACROCYCLIC COMPOUND; SARAIN A; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MARINE ENVIRONMENT; MICHAEL ADDITION; MOLECULAR INTERACTION; RING CLOSING METATHESIS; STEREOCHEMISTRY; STILLE REACTION;

EID: 34848889283     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.8b03357     Document Type: Erratum

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130. 2. For the preparation of this lithium reagent, see: D. Seyferth, S. C. Vick, J. Organomet. Chem. 1978, 144, 1-12.
131. In addition to skeletal rearrangement and loss of iodide, we have also observed fragmentation of the pyrrolidine ring (e.g., forming i), presumably through a β-elimination pathway. (Chemical Equation Presented)
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135. Nicolaou, K. C.; Ramphal, J. Y.; Abe, Y. Synthesis 1989, 898-901.
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137. Notably, the C8′ epimer of substrate 145 fails to cyclize under the identical reaction conditions.
138. The proximal tertiary amine could intercept an activated alcohol derivative prior to oxidation to afford quaternary ammonium salt ii. We postulate that this ammonium salt formed during attempted Swern oxidation of alcohol 147. (Chemical Equation Presented)
139. Dess-Martin periodinane was freshly prepared using Schreiber's procedure; see: Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549-7552.
140. Gordon, D. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 659-663.
141. For the use of TMSI to remove benzylic protecting groups, see: Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761-3764.
142. HI addition adducts were detected by ESI-MS.
143. 2D; see reference 2c.