The natural product (-)-N-methylwelwitindolinone C isothiocyanate is isolated from a blue-green algae and has been identified as a promising compound to treat drug-resistant tumors. Compound X (R = protecting group) was utilized as a key synthetic intermediate in the synthesis of the natural product (J. Am. Chem. Soc. 2011, 133, 15797-15799). Compound X can be prepared in a ring-forming reaction from compound Y under strongly basic conditions (excess NaNH2), as illustrated in the following retrosynthetic scheme: CI N-methyl- welwitindolinone C Isothiocyanate SCN ° H RO Several steps OR H H 0 Propose a plausible mechanism for conversion of Y into X under basic conditions. For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph.

The natural product (-)-N-methylwelwitindolinone C isothiocyanate is isolated from a blue-green algae and has been identified as a promising compound to treat drug-resistant tumors. Compound X (R = protecting group) was utilized as a key synthetic intermediate in the synthesis of the natural product (J. Am. Chem. Soc. 2011, 133, 15797-15799). Compound X can be prepared in a ring-forming reaction from compound Y under strongly basic conditions (excess NaNH2), as illustrated in the following retrosynthetic scheme: CI N-methyl- welwitindolinone C Isothiocyanate SCN ° H RO Several steps OR H H 0 Propose a plausible mechanism for conversion of Y into X under basic conditions. For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer. Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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